PMC:4264129 / 163552-168174 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":"3.3.3. 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 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