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

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Experimental Evidence of Intramolecular CAr–H···O=C Hydrogen Bonds in the Structure of (Diaryl)tetrahydrofuranones Using Spectroscopic Tools. / Semenok, Dmitrii V.; Medvedev, Jury J.; Avdontceva, Margarita S.; Selivanov, Stanislav I.; Sieler, Joachim; Mereshchenko, Andrey S.; Nikolaev, Valerij A.

In: Helvetica Chimica Acta, Vol. 99, No. 9, 30.07.2016, p. 716-723.

Research output: Contribution to journal › Article › peer-review

BibTeX

@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 = jul,

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",

}

RIS

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 -

ID: 7604771