PMC:4264129 / 138926-179001 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/4264129","sourcedb":"PMC","sourceid":"4264129","source_url":"http://www.ncbi.nlm.nih.gov/pmc/4264129","text":"3.3. 6-Member Rings\n\n3.3.1. β-Substituted Ethylamines\nTwo members of this family, 2-aminoethanol and ethylenediamine, capable of forming five-member rings for developing an intramolecular H-bond were already investigated in Subsection 3.2.1. Further members of the family with some having aromatic rings in the β-position which allow for H+…π interactions with protonated species will be surveyed here (Figure 8). Indeed, these ethylamines belong to the group of the extremely important neurotransmitters, which overwhelmingly adopt the amino N-protonated form at pH = 7.4, where they are involved in biological signal-transduction processes. Nonetheless, neurotransmitters maintain some small percent of the neutral form even at this pH, and create another zero-net-charge species, the zwitterionic structure up to 7.2% in total for the two forms for molecules b-e in Figure 8 [123,192]. These protonation states [193], more abundant at higher pH, will also be discussed below.\nFor histamine, formation of an intramolecular H-bond between the ethylamine side chain and the N1 nitrogen of the imidazole ring is feasible both in the neutral and the protonated forms. In cases of norepinephrine and epinephrine, an OH group, as another β-substituent is also found in the molecule. For these two latter, O–H…N and N–H+…O bridges can be formed in five-member rings for the neutral and protonated species, respectively. Furthermore, an N(amine)–H… π or an N(amine)–H+…π intramolecular H-bond is always possible for each molecule in Figure 8. The methods applied to the gas-phase and in-solution structure analyses are summarized in Table 2.\nHistamine (2-(1H-imidazol-4-yl)ethanamine). Details regarding the challenges posed by the tautomerization of this molecule were provided recently [22]. This review remains focused on aspects associated with the intramolecular H-bond formation. The rotational spectrum of gas-phase histamine was recorded by Vogelsanger et al. [194]. Four major conformations were identified, all of which are stabilized by intramolecular H-bonds involving a gauche ethylamine side-chain. These conformers encompass the N1H–N3H tautomerization for the imidazole ring and both H-bond donor and acceptor properties of the imidazole as well as of the amino group. For protonated histamine, two major gas-phase isomers were detected by Lagutschenkov et al., in the IR spectrum [195]. The more stable one is protonated on the ring and a N1(ring)-H+…N(amine) H-bond is formed. This structure is more stable by a few kJ/mol than the N1…+HN(amine) state formed by proton jump from the ring to the amino group. Both protonation forms can preferably create H-bonding within a gauche ethylamine side-chain conformation.\nFigure 8 Neurotransmitters portrayed in the neutral form: (a) Histamine; (b) Tyramine; (c) Dopamine; (d) Norepinephrine (R=H), Epinephrine (R=CH3); and (e) Serotonin. In this paper, Lagutschenkov et al., provided an excellent overview of the present status of histamine-structure research. The histamine problem is threefold: Protonation state, prevailing tautomer and conformations. If the neutral and the monoprotonated structures are separately investigated, the problem becomes twofold. The amine pKa is 9.75–9.80, so neutral histamine must be the major species in aqueous solution when it is dissolved in pure water. The solute becomes protonated only to a very small degree under such conditions, but then becomes the prevalent species at pH = 7.4.\nijms-15-19562-t002_Table 2 Table 2 Comprehensive summary of the applied experimental and theoretical methods for the conformational/tautomeric equilibria of neurotransmitters in aqueous solution a. a In cases, when more than one quantum mechanical methods were used, the level producing the best result is indicated. The “+” sign indicates that ZPE/Gth was calculated; b Reference [57]; c Reference [59]; d Reference [52]. Calculations to date show no consensus regarding the structure of the neutral histamine in aqueous solution. Karpińska et al., [196] using the continuum solvent SCRF method at the MP2/6-31G//MP2/6-31G level found the N3H tautomer as the most stable without an intramolecular H-bond. The next stable structure is higher in energy by only 0.8 kJ/mol, where the ring proton of the N1H tautomer is the H-bond donor to the amino group of the gauche ethylamine side chain. Nagy et al., [198] found the N3H tautomer with predominantly (83%) trans ethylamine side-chain conformation as the most stable structure on the basis of MP2/6-311++G**//HF/6-31G* + MC/FEP calculations. This structure prevents the formation of an intramolecular H-bond in an aqueous solution. The second most stable form, N3H/gauche ethylamine chain, is present at 12%.\nIn contrast to the above results, Ramirez et al., [199] predicted the N3H/gauche side-chain conformation to be predominant at the PCM/B3LYP/6-311G** level. Raczyńska et al., [200] performed theoretical calculations utilizing the PCM approach at the HF, MP2, and B3LYP levels with basis sets up to 6-311++G**. The prediction is a gauche-trans equilibrium for the neutral N1H tautomer in aqueous solution. Forti et al., [201] published recently a paper describing a multilevel strategy for the exploration of the conformational flexibility of small molecules. The predicted trans/gauche ratio strongly depends on the applied basis set, changing from 64/36 to 48/52 when the B3LYP/6-31G*, MP2/aug-cc-pvdz and MP2/aug-cc-pvtz theoretical levels are considered. On the other hand, the N1/N3 ratio was predicted consistently as 48:52. In summary, structure predictions for the neutral histamine in aqueous solution have not been able to form a consensus.\nThe agreement is much better regarding the monoprotonated species [196,198,200,202]. All these calculations favor the N3H tautomer in combination with a protonated ethylamine side-chain. When the side-chain conformation was also investigated, the predominant gauche structure forms an intramolecular N1…+HN(amine) H-bond. Thus the stability order differs from that in the gas phase where this species is only the second most stable structure.\nAn experimental conformational analysis in aqueous solution was performed by Kraszni et al. [197]. These authors determined the position-specific standard 1H NMR coupling constants for the gauche and trans conformers. This study helped predict the population of the trans conformer to be 41%, 38%, and 50% in neutral, monocationic and dicationic forms, respectively.\nTyramine (4-(2-aminoethyl)phenol). A good summary of recent gas-phase experiments for studying the structure of ethylamine derivatives with β-phenol and catechol substituents was provided by Ishiuchi et al. [218]. For tyramine, the gas-phase conformations were determined by Melandri and Maris [203] using a free-jet microwave study. The authors found four structures where the side-chain adopts the C(ring)–C–C–N gauche conformation and where an N–H…π H-bond may stabilize the structure. The four structures differ in the relative rotational positions of the –NH2 and the OH groups. MP2/6-31G* calculations predicted an energy range of 1 kJ/mol for these conformers. With a trans side-chain, the lowest relative energy is 5 kJ/mol.\nNagy et al., [123,204] studied tyramine theoretically in the gas-phase and in aqueous solution. Although the conformer energies of the neutral form with gauche and trans chains hardly differed as calculated at the B3LYP/6-31G* level, the free energy at T = 298 K was lower by 1.8 kJ/mol for the trans structure, in contrast to experimental data. Tyramine may form an N–H…π intramolecular H-bond in the case of the gauche side-chain conformation. The B3LYP method is known to fail accounting for dispersion interactions. On this basis, one may think that the lack of considering dispersion interactions in [123] led to the prediction of the absence of an intramolecular H-bond, which would have been stabilized by favorable and remarkable dispersion interactions otherwise. Not accounting for dispersion interactions may be the major the reasons for the trans preference, because these kinds of interactions are more important between the NH2 group and the ring than their role in stabilizing an intramolecular H-bond. The distance between the amino group and the ring is smaller in the gauche than in the trans conformation; consequently a missed account of dispersion contributions to the conformer stabilizing energy terms would more sensitively affect the gauche than the trans form. Indeed, MP2/6-31G* calculations by Melandri and Maris above, where the dispersion interactions are considered, clearly indicate the gauche preference.\nIn aqueous solution at physiological pH 7.4, the protonated form is present at about 99% [204]. For this structure, the only stabilization possible is when the –CH2–CH2–NH3+ chain bends above the aromatic ring, forming an N–H+…π intramolecular H-bond. Also in the solution are two zero-net charge forms, zwitterionic (zw) and neutral (neu), in a total population slightly more than 1%. The zw: neu ratio rapidly decreases from 10.72 to 2.45 in aqueous solution when the temperature is raised from 14 to 37 °C [123]. Nonetheless, the zw form must be the prevalent zero-net-charge structure when tyramine dissolves in pure water at room temperature. Theoretical calculations at the PCM/MP2/6-31G*//B3LYP/6-31G* level found the neu form prevalent. In contrast, using the MC/FEP method, the zw form is the stable overall neutral tautomer, although the relative free energy is much exaggerated in comparison with the derivable experimental value [123].\nDopamine (4-(2-Aminoethyl)benzene-1,2-diol). Cabezas et al., [205] found experimentally seven conformers for the gas-phase (neutral) dopamine. All structures maintain an O–H…O H-bond on the benzene ring. The ethylamine side-chain has a gauche C(ring)–C–C–N conformation. The seven structures come into existence with N–H…π interactions in different rotational positions of the –NH2 group relative to the O–H…O bond. Lagutschenkov et al. [208] recorded the gas-phase IR spectrum for protonated dopamine. Not surprisingly, the protonated side-chain in the most stable conformers adopts the gauche arrangement as defined above for the neutral form and bends above the aromatic ring. This interaction corresponds to a N–H+…π intramolecular H-bond. The authors performed B3LYP and MP2 calculations using the cc-pvdz basis set and concluded that the H-bond on the ring is of O(3)–H…O(4) type in the two lowest energy structures, separated only by 0.1 kJ/mol in free energy.\nOther theoretical studies in the literature also found a H-bonded 3-OH/4-OH substructure, nearly coplanar with the ring both in the gas phase and aqueous solution, see, e.g., [123,206,209]. Šolmajer et al., [207] studied the protonation process experimentally for several neurotransmitters, including dopamine. The protonated form stably exists up to about pH = 8 and then the proton is gradually lost in the pH range of 8–10. Less than 5% of the amines remain protonated above pH = 11.5. The ethylamine side-chain may adopt three main conformations along the C(ring)–C–C–N path. Two, nearly equal-energy gauche and one trans conformations are stable, with different rotational positions for the neutral –NH2. An intramolecular H-bond in the form of N–H…π or N–H+…π is possible only in the gauche conformation of the side-chain.\nBoth the neutral and a zwitterionic zero-net-charge structures are present in aqueous solution, where one of the hydroxy protons jumps to the –NH2 group or (more likely) the zwitterion gets formed by water catalysis. Although the population of the zero-net-charge form is pH dependent and is present in a total of only about 3% at pH = 7.4, the neu:zw ratio of about 10 must be constant in any aqueous solution [204]. By performing MC/FEP solvent-effect calculations, Nagy et al., [123] predicted that the proton comes from the 4-OH group in the zwitterion, still maintaining the O(3)–H…O(4) intramolacular bond on the benzene ring. The related conformation of the ethylamine side-chain is preferably trans. For the protonated dopamine, the ratio of the gauche (G) and trans (T) side-chains in aqueous solution was calculated by Nagy et al., [209] theoretically, using HF/6-31G* relative internal energies and MC/FEP simulations for estimating the solvent effect. The predicted G:T ratio of at least 75:25 is somewhat comparable with the experimentally found value of 58:42 at pH = 7 [207].\nNorepinephrine (4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol), is a derivative of the 2NH2-ethanol with a 3,4-dihydroxyphenyl substituent at C1 of the ethane chain. The gas-phase structure of the neutral norepinephrine (with older name: Noradrenaline) was studied by Snoek et al. [210]. The authors found that almost the entire population of jet-cooled noradrenaline adopts a conformation with extended ethanolamine side-chain allowing for a H-bond between the side-chain OH and the amino group, as well as between the phenolic hydroxyls.\nThe prevailing structure is the protonated form in physiological systems, 92.8% at pH = 7.4 [192]. An N–H+…O intramolecular H-bond is favorable, which can exist in one of the C(ring)–C–C–N gauche conformations and in the trans form. In the other gauche conformation, where the formation of the N–H+…O bond is prevented because of the local O–C–C–N trans arrangement, the possible conformer-stabilizing effect through the N-H+… π interaction should be emphasized. The two phenolic OH groups form a hydrogen bond like in the gas phase, but probably only on the basis of the distance criterion, since Mandado et al., [7] did not find a (3, −1) BCP for 1,2-dihydroxybenzene.\nThe equilibrium conformer fractions were calculated at the ab initio and DFT levels using the PCM continuum solvent approach and the FEP method in MC simulations [192]. The method applied for calculating the relative internal free energies affect the final conclusions. Overall, the internally bound OCCN conformers were found to dominate the composition in fair agreement with experimental findings at pH = 7 [207].\nUsing the PCM method, Alagona and Ghio [211] studied the conformer population for neutral and protonated norepinephrine in aqueous solution at the HF/6-31G* and MP2/6-31G*//HF/6-31G* levels. The calculated T fraction regarding the C(ring)–C–C–N torsion of the neutral form is 61%–72%, whereas the trans form was populated experimentally by about 59% (pH = 11.5). The T:G ratio for the protonated species was calculated as 89:11 and 44:56 at the HF and MP2 levels, respectively, in comparison with the experimental composition of 65:35 at pH = 7.0 [207].\nEpinephrine ((R)-4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol). Epinephrine (with its older name, adrenaline) is the N-methyl derivative of norepinephrine. Its gas-phase structure was studied by a combination of mass-selected ultraviolet and infrared holeburn spectroscopy [212]. The identified conformation has an extended side-chain structure with an intramolecular O–H…N H-bond. The authors also identified experimentally the H-bonded substructure for the two phenolic OH groups.\nEpinephrine is only slightly soluble in water and alcohol, but is readily soluble in aqueous solution of mineral acids. At pH = 7.4 only the protonated form, 94.8% [204], should be the subject of theoretical calculations. Alagona and Ghio [213] studied the conformational equilibrium for protonated adrenaline in aqueous solution at the DFT and ab initio MP2 levels and using the IEF-PCM solvation approximation. The C(ring)–C–C–N trans arrangement (corresponding to a gauche OCCN arrangement) was found as the most stable conformation allowing for the O…+H–N H-bond but preventing the H+…π interaction with the catechol ring. The two OH groups on the benzene ring maintain the O–H…O H-bond in aqueous solution.\nThe OCCN trans conformation was found to be only 10% in the experimental composition at pH = 9 for norepinephrine [207]. The corresponding value for ephedrine is 13%. Ephedrine is structurally related to epinephrine, bearing an N-methyl group, as well, but missing phenolic hydroxy groups and with an additional methyl group on the ethyl chain. Overall, the H-bond pattern for epinephrine is expected to be similar to that for norepinephrine.\nSerotonin (5-Hydroxytryptamine). LeGreve et al., [214] investigated the gas-phase serotonin conformers using different spectroscopic methods. They identified eight neutral serotonin conformers including the side-chain both in C(ring)–C–C–N gauche and anti (trans) conformations, and two main rotational positions for the OH group. The most populated conformation is Gpy(out)/anti OH, where the gauche side-chain is on the pyrrole side of indole, one of the NH2 hydrogens points toward the pyrrole nitrogen, and the indole (N)H is in anti position with respect to the hydroxy hydrogen. Thus the intramolecular H-bond is basically of an N–H…π type.\nLagutschenkov et al., [215] recorded the gas-phase IR spectrum of protonated serotonin. They found a gauche conformation for the protonated ethylamine side-chain rotated toward and above the phenolic ring of the indole moiety. In this position, N–H+…π, cation…π interaction stabilizes the structure. The preference of this conformation was supported by B3LYP and MP2 calculations.\nNagy et al., [192] calculated the distribution of the zero-net-charge forms, neutral (neu) and zwitterionic (zw), for serotonin at pH = 7.4. In that solution, the protonated form is present at 99.7%, and the zero-net-charge form is present only at about 0.3%. However, since the determined neu:zw ratio of about 1.2 is pH independent, if serotonin is still non-protonated when dissolved in aqueous solution, the above neu:zw ratio should hold for the major zero-net-charge protonation state.\nAlagona and coworkers studied the conformational equilibrium for the protonated serotonin in aqueous solution [216,217]. According to the covalent structure of the molecule, the only possible intramolecular H-bond is of N–H+… π type, similar to that for tyramine and dopamine (not considering the stably maintained O-H…O bond for the latter.) For such systems, the correct prediction of the gauche-trans conformational equilibrium for the side-chain is crucial. For histamine, norepinephrine and epinephrine, the side-chain conformation is probably more effectively dictated by the possible formation of N–H+…N and N–H+…O H-bonds.\nThe serotonin study in [216] shows almost all computational difficulties emerging throughout the conformational analysis for solutes. The obtained relative internal energy results depend on the level of theory used during the calculations. Contributions of the relative thermal corrections to the total relative conformational free energies are critical. It has also revealed that the solvation method, thus whether the relative solvation free energy was calculated at the PCM level or in a MC/FEP process, has an effect on the final results. Should the counterion be allowed to freely move in the solution in MC simulations, or a fixed solute-counterion separation is acceptable for expediting the FEP calculations? Are atomic charges more preferable from CHELPG or RESP fit to the in-solution MEP?\nDue to the listed problems, the results from the above study were not conclusive. Different combinations of the relative free energy components, calculated on the basis of the IEF-PCM/B3LYP/6-31G* and IEF-PCM/MP2-6-31G*//B3LYP/6-31G* levels for the internal terms and using MC/FEP relative solvation free energies, could lead to the preference for either the trans or gauche side-chain conformations. In the absence of experimental data, the “best” choice was not clear. Nonetheless, all calculations predicted an observable equilibrium between gauche and trans side-chain conformations, since the total relative free energies were within a range of about 4 kJ/mol.\nBy performing an IEF-PCM analysis for the solution phase, Alagona and Ghio [217] studied the protonated serotonine conformations in the gas phase and in water solvent. The potential curve at MP2/6-31G* level in the gas phase for the hydroxy hydrogen rotation shows that the hydrogen atom is syn to the indole (N)H. The IEF-PCM/MP2/6-31G*//MP2/6-31G* free energy in solution is more negative by 5.3 kJ/mol for the gauche conformer with the –NH3+ group rather away (G1) than toward (G2) the indole ring. The trans form is higher in free energy by 1.5 kJ/mol than G2. These calculations predict the overwhelming presence of the two gauche conformers in aqueous solution in comparison with the trans structure.\nIn conclusion, the intramolecular H-bond in aqueous solution is generally maintained either in the form of NH+…X (X = O, N) or through NH+…π interactions for neurotransmitters with a protonated amino group. For the neutral structures in this phase, the theoretical calculations have led to different conclusions. The neutral form is prevalent generally at pH \u003e 9, where all studied neurotransmitters possessing at least one phenolic OH can adopt also the zwitterionic form in aqueous solution. The pH independent neu:zw ratio is largely varying at T = 298 K, from about 0.2 for tyramine to 1.2 for serotonine and to about 10 for dopamine.\n\n3.3.2. β-OH Carboxylic Acids\n2-COOH phenol. Salicylic acid is the classical β-OH carboxylic acid in the aromatic series. It was already discussed in Section 3.2.3 as a phenol derivative. The primary structural difference between an aromatic and an aliphatic β-OH carboxylic acid is that the heavy atoms are coplanar for the aromatic molecule unless a neighboring substituent forces the –COOH group to rotate out of the benzene plane. In the case of a coplanar skeleton like 2-COOH phenol, both =O…H–O and O–H…O–H intramolecular H-bonds are conceivable. For the latter type, the donor hydrogen can come from either hydroxy group.\nAliphatic acids. In contrast to aromatic systems, the C(carboxylic)CCO moiety would generally adopt a (nearly) gauche or trans conformation in the aliphatic series. Unfortunately, no calculations analyzing structure were found for the simplest β-hydroxy carboxylic acid, namely β-hydroxy propionic acid. Its α-amino derivative, serine (α-amino, β-hydroxy propionic acid) was studied as an α-amino acid above. Seven low-energy conformers of l-threonine ((2S,3R)-2-amino-3-hydroxybutyric acid), the β-methyl derivative of serine, were identified in the gas phase by Alonso et al. [219]. In the lowest energy conformation, the alcohol OH is a proton donor to the NH2 group, as it was found for 2-NH2 ethanol. This bond clearly does not exist for a simple β-hydroxy acid. In the second lowest energy structure (34 cm−1, 0.4 kJ/mol above the minimum, as calculated at the MP2/6-311++G** level) the alcohol OH forms a H-bond to the carbonyl oxygen of the anti carboxylic group. Because the NH2 group also serves as a competing H-bond acceptor, it did not reveal whether an O–H…O= bond is also feasible to the syn –COOH group. Geometry results indicate, however, that this interaction could easily come into existence.\nA combined spectroscopic and in-solution quantum chemical investigation was carried out by Quesada-Moreno [220] at pH = 1.00, 5.70 and 13.00 in aqueous solution, and the protonation states of the molecule were modeled theoretically under the experimental conditions. The conformational search found 9 zwitterions, 27 anions and 52 cations at the B3LYP/6-311++G(d,p) level of theory, whereas the most stable conformers were optimized at the M062X/6-311++G(d,p) and MP2/6-311++G(d,p) levels of theory, as well. The solvent effects were calculated by means of the IEF-PCM method. As the authors write: “With regard to the zwitterion, the importance of the analysis of the low frequency region (700–30 cm−1) in the Far-IR spectra should be noted, because it provides relevant information that can be used to determine the presence of the most stable structures.”\nDiscussion of the large number of conformations is beyond the possibilities of this review. Regarding the possible H-bonds between the carboxylic and OH groups, conformers of the protonated species may be informative. For this species the –COOH group is not ionized. The presented, low energy conformations are dominated, however, by –NH3+…O hydrogen bonds (sometimes to two oxygens at the same time) and perhaps only higher-relative-energy conformers would show H-bonds between the carboxylic and OH groups. Related geometries are not provided in the paper, and the reader is advised to turn to the authors directly.\n\n3.3.3. β-NH2 Carboxylic Acids\nStructural results have been found as prototypes for the aliphatic and aromatic β-NH2 carboxylic acids. On the basis of the rotational spectrum for β-amino propionic acid (β-alanine), McGlone and Godfrey [221] concluded that there are two conformers in the gas phase which are similar to those assigned for glycine as conformers I and II and correspondingly to α-alanine. This means that the systems are not sensitive to whether an intramolecular H-bond is formed in a five-member ring (glycine, α-alanine) or in a six-member ring as for β-alanine. Sanz et al., [222] found two more conformers, where the symmetrical Gly I-like form is disrupted into two, non-symmetrical structures with different N–H…O= bonds. A fourth conformation was identified as stabilized by an n→π * interaction involving the nitrogen lone pair and the π * orbital of the carbonyl group.\nThe in-solution structure of β-alanine was recently studied by Nagy [89] in water and chloroform solvents. The α-amino acids are known to take predominantly the zwitterionic form in aqueous solution. Nagy investigated whether the NH3+…−OCO form is also stable in aqueous solution, or if the proton jumps over onto the carboxylate group in the gauche NCCC conformation. Calculating the relative internal free energy of the conformers/tautomers at the B97D/aug-cc-pvtz level, and determining the relative solvation free energies in a MC/FEP process, the conclusion was that the gauche zwitterion is more stable by about 4 kJ/mol in aqueous solution than the gauche neutral form with an anti –COOH group forming an H2N…HOC=O intramolecular H-bond. The gauche zwitterion is more stable than the trans conformer by 24–33 kJ/mol.\nOptimizing the geometry of the gauche zwitterion in chloroform, the starting geometry was chosen as the in-water optimal structure. Through the IEF-PCM/B97D/aug-cc-pvtz optimization, the extra proton from the NH3+ group returned to the carboxylate group in an anti conformation, and the corresponding gauche neutral structure was formed. This conformer is more stable by about 17 kJ/mol than the extended trans conformer. The trans zwitterion is also a local energy minimum on the potential surface, but is higher in free energy by about 58 kJ/mol than the corresponding neutral form.\n2-NH2 benzoic acid (anthranilic acid). Upon the interpretation of the electronic and IR results for anthranilic acid in a supersonic jet [223], the existence of two anthranilic acid conformers was predicted in the gas phase. The amino group serves as a H-bond donor in both. The carbonyl oxygen is the acceptor in the more stable rotamer, whereas the N–H…O-H bond is formed in the less stable structure. Both bonds must be weak due to the weak acidity of an aniline-type –NH2 group.\nFor studying the solvent effect on the molecular structure, Abou-Zied et al., [224] recorded the absorption and fluorescent spectra of the molecule in neat and binary solvents of varying polarities and H-bonding strengths including cyclohexane, dioxane, acetonitrile, methanol, ethanol and DMSO. By titration in aqueous solution in the pH range of 2–12, the authors derived the pKa to be 4.50. They concluded that the intramolecular H-bond pattern, as found in the gas phase, is maintained and that the –NH2 group still serves as an intramolecular H-bond donor. The carboxylic group can become a member of a cyclic system where a network of three water molecules forms a bridge between the carbonyl oxygen and the acidic hydrogen. The first and third water of the network act as an intermolecular H-bond donor and acceptor to the carbonyl oxygen and the hydroxy hydrogen, respectively. The trihydrate structure was predicted on the basis of B3LYP/6-311++G(2d,p) calculations.\nIn an unpublished study, Nagy found that the zwitterionic form is not stable for this molecule in neutral water. Starting from a reasonable zwitterionic form for B97D/aug-cc-pvtz geometry optimization using the IEF-PCM continuum dielectric solvent model, the proton of the –NH3+ group jumped to the carboxylate group resulting in a O–H…NH2 intramolecular H-bond. In the light of the above results, such a structure with an anti –COOH group for anthranilic acid, even if exists in aqueous solution, must be a higher-energy conformer. Furthermore, Abou-Zied and coworkers raised the possibility of acid dimerization, which in combination with their conclusions regarding the aqueous solution structure, is more likely in non-protic solvents, e.g., in cyclohexane. The dimeric structure can come into existence favorably with the syn –COOH group for a participant.\n\n3.3.4. Cyclic Enols\nDue to the electron withdrawing effect of the oxygen atom in a C=O double bond, the hydrogen(s) on the neighboring carbon atom become(s) more acidic. As a consequence, an equilibrium emerges between the –CHx–C(R)=O and the –CH(x−1)=C(R)–OH structural forms. The equilibrium is called keto-enol tautomerism. If there are no additional polar groups in the molecule, at least not close to the carbonyl group, the equilibrium is generally shifted toward the –C=O containing structure. A more complicated situation comes into existence if two carbonyl groups are separated by a CHx (x = 1,2) unit. Typical examples are β-diketones and dialdehydes, β-keto carboxylic acids and esters, the dicarboxylic malonic acid and its esters. For such species, the keto-enol tautomerism was demonstrated experimentally by Moriyasu et al., in different polarity solvents [225]. The determined equilibrium compositions indicate that the preference of the enol structure increases in more dilute solutions but decreases with the increasing polarity of the solvent. For ethyl acetoacetate (for the gas-phase molecular structure of the methyl acetoacetate, see [226]), which is favorably used for syntheses of ketones and carboxylic acid esters, the keto form predominates in chloroform and more polar solvents. In contrast, the enol form is much more favored in all studied solvents but water for acetylacetone. With aromatic rings connected to the β-diketo moiety, the enol form is overwhelming in any studied organic solvents.\nGrabowski [2] referring to some former papers emphasized the importance of the interrelation between π-electron delocalization and H-bonding. For molecules possessing a β-diketo moiety, a favorable and coplanar six-member intramolecular H-bond can occur. The situation is similar to the case when the phenolic OH forms a H-bond to the carbonyl oxygen in 2-COOH phenol (salicylic acid). Whereas the formation of the intramolecular H-bond within a six-member ring does not need a solvent-affected keto-enol tautomeric shift for salicylic acid, formation of a H-bond donor hydroxy group is solvent dependent for a β-diketo moiety.\nMalondialdehyde. This molecule is the simplest 1,3-dicarbonyl species, actually a dialdehyde. The gas-phase microwave spectrum was recorded by Baughcum et al., [227] and the IR spectrum by Seliskar and Hoffmann [228]. The string “malonaldehyde (3-hydroxy-2-propenal)” in the title of the Buaghcum paper is noteworthy. The authors want to emphasize in the title that the system is subject to keto-enol tautomerism.\nFor β-dicarbonyl systems, a conjugated double-bond moiety comes into existence in the form of HO–CH=CHx–C=O (x = 0, 1) when the enol structure is created. Such molecules are subject to s-cis/s-trans conformational equilibrium about the formal single CHx–C bond. This type of conformational equilibrium was recently studied by Nagy and Sarver [117], who also investigated the effect of the non-polar solvents and water on the in-solution conformer composition. Structures 13 and 14 are examples for the s-cis and s-trans conformations, respectively.\nAn intramolecular H-bond can be formed only in the s-cis conformation of the enolic malondialdehyde. If the heavy atom skeleton is not entirely coplanar, the structure is called gauche, as found for the second stable form of 1,3-butadiene. The above experimental studies found fully planar molecular structure for 3-hydroxy-2-propenal, as the enol form was called in [227]. Earlier theoretical studies have been summarized by Grabowki [2] on the keto-enol tautomerism and the geometric consequences of the process.\nIf the molecule has a C2v symmetry for the planar malondialdehyde in the dicarbonyl form or C2 for acetylacetone, then two equivalent enol forms can be derived from the structure. Since the molecules are undistinguishable except, e.g., if there are different isotopes for the oxygens, the proton relocation to one or to the other oxygen cannot be noticed macroscopically. A possible reaction route is that the two OH groups are formed via the intermediate formation of the dicarbonyl structure.\nThe authors of the experimental studies [227,228] argue, however, in favor of a tunneling mechanism. The two, undistinguishable enol forms, which are now unsymmetrical, could transform into each other through a structure of C2v symmentry, where the electrons of the two double bonds are delocalized. The quantum chemical explanation for the intramolecular proton relocation rests on the acceptance of a double-well potential for the process, where the isoenergetic enol forms correspond to local energy minima, and the symmetrical intermediate structure with four delocalized electrons in a six-member ring correspond to a transition state.\nIn-solution NMR investigations were performed in chlorofom by Bothner-By and Harris [229] and by Bertz and Dabbagh [230]. Bothner-By and Harris compared a number of s-cis and s-trans conformational/tautomeric isomers, Bertz and Dabbagh listed former publications in different solvents. These studies reveal that the trans enol form of malondialdehyde (called simply trans) exists in water, protic and polar solvents, whereas the enol adopts the cis form in non-polar solvents. Bertz and Dabbagh found, however, that polar impurities like methanol affect the conformer ratio in CHCl3. The methoxy oxygen of methanol competes with the carbonyl oxygen in forming an intermolecular vs. intramolecular H-bond with the OH group. This is exactly the problem addressed in the title of this review. Bertz and Dabbagh did not consider an O–H…O intramolcular H-bond as a decisive factor in stabilizing the cis conformation.\nGeorge et al., [231] optimized six planar conformers for β-hydroxyacrolein (malondialdehyde enol) and compared the energies of the most stable cis and trans forms at the 4–31G level. They concluded that the most stable cCc conformation can create an intramolecular H-bond. In the opinion of Bertz and Dabbagh, the result in favor of the intramolecularly bound structure is not convincing enough, because possible intermolecular H-bonds with proton acceptor molecules, like methanol, have not been considered. Indeed, pointing out the disruption of the intramolecular bond in solution, consideration of gas phase hydrates/solvates would still not be enough; explicit solvent or at least supermolecule studies in continuum solvents should be performed.\nThe structures presented by Bothner-By and Harris show a number of various conformers/tautomers, which could be in equilibrium in chloroform. By considering a series of solvents listed by Bertz and Dabbagh, chloroform represents a borderline solvent between very low dielectric constant solvents like hexane and carbon tetrachloride vs. protic, highly polar solvents like methanol and water. Although Bothner-By and Harris predicted a prevalent s-trans conformation, other researcher argue in favor of the s-cis form (see for references in [230]). The conformational problem becomes even more complicated if considering that not only s-cis/s-trans conformers have to be compared, but there are two different arrangements of the OH group relative to the –CH=CH–CH=O moiety.\nIn summary, prediction of the enolic malondialdehyde conformational/tautomeric equilibrium presents a very complicated structural problem, as revealed from experiments for solutions in moderately polar solvents. Satisfactory high-level theoretical calculations for any in-solution equilibrium, which could make at least initial suggestions about the structural preference have not been found through the literature search.\nAcetylacetone. This molecule is the classical target for theoretical considerations of the keto-enol tautomerism. Belova et al., [31] found from gas-phase electron diffraction investigation 100% of the enol form at 300 K and 64% at 671 K. The enol form with CS symmetry possesses a strongly asymmetric intramolecular H-bond in the gas-phase. For aqueous solution, the CS symmetry, involving coplanar heavy atoms, has been called in question by Bothner-By and Harris [229], who mentioned that the NMR spectrum reflects the average of two, isoenergtic, non-planar molecular structures in water. The keto form is of C2 symmetry. Most of the molecular structural parameters, including the H-bond parameters and the critical O=C–C–C torsion angle for the keto form were reproduced well by B3LYP/aug-cc-pvtz and MP2/cc-pvtz calculations.\nMoriyasu et al., [225] found an enol/keto ratio of 0.34 in 0.1 and 0.01 molar aqueous solutions at T = 298 K. Other experiments (for references, see Alagona et al. [232]) predict 0.14 as the lower limit. This suggests that although the enol form exists in aqueous solution, its fraction is much reduced even compared with its population at T = 671 K in the gas phase. On the basis of the experimental equilibrium compositions, the standard state free energy difference for the enol and keto forms is 2.7–4.9 kJ/mol. A number of recent theoretical in-solution studies have been performed for acetylacetone in order to reproduce this experimental value. Although any calculation predicted both stable enol and keto structures, their predicted ratio scattered considerably.\nIshida et al., [233] succeeded to closely reproduce the lower limit of the experimental data by performing RISM-SCF calculations in water. The general reliability of the method is questionable, however, if considering that the predominant gas-phase structure was not correctly predicted and the prevailing tautomer was strongly overestimated in carbon tetrachloride. Schlund et al., [234] calculated enol preference in aqueous solution and concluded that if the PCM model is used, the majority of the diketo form cannot be reproduced. Accordingly, Alagona et al., [232] used the IEF-PCM method at different theoretical levels only for estimating the relative internal free energy. The relative solvation free energy was predicted by means of the MC/FEP method. The calculated best in-water total free energy difference was 0.7 kJ/mol, corresponding to enol/keto ratio of 0.75.\nRelated systems. Six-member rings with an intramolecular H-bond have been found for a number of systems such as 2-phenyliminomethyl-naphthalen-l-ol [235,236], its isomer, 1-phenyliminomethyl-naphthalen-2-ol, and substituted 3-hydroxy-4-pyridaldehyde deivatives [237]. For these molecules, the covalent structure assures the possibility of the intramolecular hydrogen bond in some preferable conformation. The authors concentrated, however, on the tautomeric issue, thus whether an N–H…O= or an =N…H–O hydrogen bond is more stable under the conditions in solution. These studies are mentioned here only as related systems, because the authors did not investigate the possible disruption of the intramolecular H-bond.\n","divisions":[{"label":"Title","span":{"begin":0,"end":19}},{"label":"Section","span":{"begin":21,"end":21305}},{"label":"Title","span":{"begin":21,"end":53}},{"label":"Figure caption","span":{"begin":2727,"end":2896}},{"label":"Table 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