Infrared study of hydrogen bonds involving N‐heterocyclic bases and phenols
- 1 January 1999
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 36 (1) , 49-55
- https://doi.org/10.1002/jhet.5570360109
Abstract
The hydrogen bond complexes between phenols and N‐heteroaromatic bases 2,4,6‐tri(2‐pyridyl)‐1,3,5‐triazine, 2,2′,2′‐terpyridine, quinoxaline, pyrido[2,3‐b]pyrazine, pyzazino [2,3f]quinoxaline and 5‐nitrozphenanthroline are investigated by infrared spectroscopy in 1,2‐dichloroethane. The stability constants of the complexes involving N‐heteroaromatic bases characterized by tow vicinal nitrogen atoms having lone pairs pointing to each other are higher than predicted from their basicity. Possible differences between protonation and hydrogen bond formation are discussed. Nheteroaromatic bases such as tri(2‐pyridyl)‐1,3,5‐triazine or phenanthrolines cannot be considered as proton sponges but their behaviour is intermediate between that of the classical heteroaromatic bases and the proton sponges.Keywords
This publication has 29 references indexed in Scilit:
- FT-IR (7500−1800 cm-1) Study of Hydrogen-Bond Complexes between Phenols−OH(OD) and Pyridine. Evidence of Proton Transfer in the Second Vibrational Excited StateThe Journal of Physical Chemistry A, 1997
- Conformers, Energetics, and Basicity of 2,2‘-BipyridineJournal of the American Chemical Society, 1996
- Infrared study of hydrogen bonds involving 2,2′-bipyridine and 2,2′-bipyrimidine. Influence of equivalent nitrogen atoms on the hydrogen bond strengthSpectrochimica Acta Part A: Molecular Spectroscopy, 1992
- A spectroscopic study of the iodine complexes of donors—pyridines, phenanthrolines, bipyridines and diazinesSpectrochimica Acta Part A: Molecular Spectroscopy, 1990
- Inftared study of the interaction between proton donors and 1,10-phenanthroline derivativesSpectrochimica Acta Part A: Molecular Spectroscopy, 1989
- Hydrogen bond equilibria of phenol-pyridine in cyclohexane, carbon tetrachloride, and benzene solventsThe Journal of Physical Chemistry, 1987
- Study of monoprotonated nitrogen bases using x-ray photoelectron spectroscopy (ESCA)Journal of the American Chemical Society, 1972
- Fermi resonance in hydrogen bondingSpectrochimica Acta Part A: Molecular Spectroscopy, 1967
- Stretching Frequencies as a Function of Distances in Hydrogen BondsJournal of the American Chemical Society, 1955
- Spectroscopic Studies of the Hydrogen Bond. II. The Shift of the O–H Vibrational Frequency in the Formation of the Hydrogen BondThe Journal of Chemical Physics, 1937