Influence of hydrogen bonds on edge-to-face interactions between pyridine molecules

• Published in: Journal of molecular modeling 2018-03, Vol.24 (3), p.60-10, Article 60
• Main Authors: Andrić, Jelena M., Antonijević, Ivana S., Janjić, Goran V., Zarić, Snežana D.
• Format: Article
• Language: English
• Subjects: Bonding strength; Characterization and Evaluation of Materials; Chemical bonds; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Dimers; Hydrogen; Hydrogen bonding; Hydrogen bonds; Hydrogen-based energy; Mathematical analysis; Molecular Medicine; Original Paper; P. Politzer 80th Birthday Festschrift; Pyridines; Theoretical and Computational Chemistry
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-017-3570-y

Edge-to-face interactions between two pyridine molecules and the influence of simultaneous hydrogen bonding of one or both of the pyridines to water on those interactions were studied by analyzing data from ab initio calculations. The results show that the edge-to-face interactions of pyridine dimers that are hydrogen bonded to water are generally stronger than those of non-H-bonded pyridine dimers, especially when the donor pyridine forms a hydrogen bond. The binding energy of the most stable edge-to-face interacting H-bonded pyridine dimer is −5.05 kcal/mol, while that for the most stable edge-to-face interacting non-H-bonded pyridine dimer is −3.64 kcal/mol. The interaction energy data obtained in this study cannot be explained solely by the differences in electrostatic potential between pyridine and the pyridine–water dimer. However, the calculated cooperative effect can be predicted using electrostatic potential maps.