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Experimental Evidence of Intramolecular C Ar –H···O=C Hydrogen Bonds in the Structure of (Diaryl)tetrahydrofuranones Using Spectroscopic Tools
Author(s) -
Semenok Dmitrii V.,
Medvedev Jury J.,
Avdontceva Margarita S.,
Selivanov Stanislav I.,
Sieler Joachim,
Mereshchenko Andrey S.,
Nikolaev Valerij A.
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201600149
Subject(s) - chemistry , intramolecular force , tetrahydrofuran , hydrogen bond , molecule , crystallography , solvent , polarity (international relations) , spectral line , stereochemistry , biochemistry , organic chemistry , cell , physics , astronomy
The occurrence of bifurcate H‐bonds C Ar –H···O=C in the structure of (diaryl)‐tetrahydrofuranones was experimentally demonstrated using different methods and techniques. The consistent increasing spin–spin coupling constants 1 J (C,H) of the ortho ‐H‐atoms and low‐field shift of v C=O in IR spectra of 2,2‐(diaryl)tetrahydrofuran‐3(2 H )‐ones relative to their 5,5‐diaryl counterparts, as well as pronounced dependence of the ortho ‐C–H H‐atoms chemical shifts on the temperature and solvent polarity along with X‐ray diffraction analysis data unambiguously point to the existence of weak C Ar –H···O=C H‐bonds in these molecules.