Experimental Evidence of Intramolecular CAr–H···O=C Hydrogen Bonds in the Structure of (Diaryl)tetrahydrofuranones Using Spectroscopic Tools

Dmitrii V. Semenok, Jury J. Medvedev, Margarita S. Avdontceva, Stanislav I. Selivanov, Joachim Sieler, Andrey S. Mereshchenko, Valerij A. Nikolaev

Research output

3 Citations (Scopus)

Abstract

The occurrence of bifurcate H-bonds CAr?H···O=C in the structure of (diaryl)-tetrahydrofuranones was experimentally demonstrated using different methods and techniques. The consistent increasing spin?spin coupling constants 1J(C,H) of the ortho-H-atoms and low-field shift of vC=O in IR spectra of 2,2-(diaryl)tetrahydrofuran-3(2H)-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 CAr?H···O=C H-bonds in these molecules.
Original languageEnglish
Pages (from-to)716-723
Number of pages8
JournalHelvetica Chimica Acta
Volume99
Issue number9
DOIs
Publication statusPublished - 30 Jul 2016

Cite this

@article{e6e8ef110cb14c6b9e54f77260de6699,
title = "Experimental Evidence of Intramolecular CAr–H···O=C Hydrogen Bonds in the Structure of (Diaryl)tetrahydrofuranones Using Spectroscopic Tools",
abstract = "The occurrence of bifurcate H-bonds CAr?H···O=C in the structure of (diaryl)-tetrahydrofuranones was experimentally demonstrated using different methods and techniques. The consistent increasing spin?spin coupling constants 1J(C,H) of the ortho-H-atoms and low-field shift of vC=O in IR spectra of 2,2-(diaryl)tetrahydrofuran-3(2H)-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 CAr?H···O=C H-bonds in these molecules.",
keywords = "Diazoketones, Furanones, IR Spectroscopy, Variable-temperature NMR, Weak hydrogen bond, X-ray diffraction analyses",
author = "Semenok, {Dmitrii V.} and Medvedev, {Jury J.} and Avdontceva, {Margarita S.} and Selivanov, {Stanislav I.} and Joachim Sieler and Mereshchenko, {Andrey S.} and Nikolaev, {Valerij A.}",
note = "doi: 10.1002/hlca.201600149",
year = "2016",
month = "7",
day = "30",
doi = "10.1002/hlca.201600149",
language = "English",
volume = "99",
pages = "716--723",
journal = "Helvetica Chimica Acta",
issn = "0018-019X",
publisher = "Wiley-Blackwell",
number = "9",

}

TY - JOUR

T1 - Experimental Evidence of Intramolecular CAr–H···O=C Hydrogen Bonds in the Structure of (Diaryl)tetrahydrofuranones Using Spectroscopic Tools

AU - Semenok, Dmitrii V.

AU - Medvedev, Jury J.

AU - Avdontceva, Margarita S.

AU - Selivanov, Stanislav I.

AU - Sieler, Joachim

AU - Mereshchenko, Andrey S.

AU - Nikolaev, Valerij A.

N1 - doi: 10.1002/hlca.201600149

PY - 2016/7/30

Y1 - 2016/7/30

N2 - The occurrence of bifurcate H-bonds CAr?H···O=C in the structure of (diaryl)-tetrahydrofuranones was experimentally demonstrated using different methods and techniques. The consistent increasing spin?spin coupling constants 1J(C,H) of the ortho-H-atoms and low-field shift of vC=O in IR spectra of 2,2-(diaryl)tetrahydrofuran-3(2H)-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 CAr?H···O=C H-bonds in these molecules.

AB - The occurrence of bifurcate H-bonds CAr?H···O=C in the structure of (diaryl)-tetrahydrofuranones was experimentally demonstrated using different methods and techniques. The consistent increasing spin?spin coupling constants 1J(C,H) of the ortho-H-atoms and low-field shift of vC=O in IR spectra of 2,2-(diaryl)tetrahydrofuran-3(2H)-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 CAr?H···O=C H-bonds in these molecules.

KW - Diazoketones

KW - Furanones

KW - IR Spectroscopy

KW - Variable-temperature NMR

KW - Weak hydrogen bond

KW - X-ray diffraction analyses

U2 - 10.1002/hlca.201600149

DO - 10.1002/hlca.201600149

M3 - Article

VL - 99

SP - 716

EP - 723

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

SN - 0018-019X

IS - 9

ER -