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Infrared study of hydrogen bonds involving N-heterocyclic bases and phenols

✍ Scribed by Muriel Goethals; Thérese Zeegers-Huyskens; Boguslawa Czarnik-Matusewicz

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
409 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

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 [2,3__f__]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. __N__heteroaromatic 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.

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