Intramolecular Hydrogen Bonding in (2-Hydroxybenzoyl)benzoylmethane Enol

Bjarke Knud Vilster Hansen, Morten Winther, Jens Spanget-Larsen

Research output: Other contributionNet publication - Internet publicationResearch

Abstract

In the stable enol tautomer of the title compound (OHDBM), one carbonyl group is flanked by two β-hydroxy groups, giving rise to bifold intramolecular H-bonding. A similar situation is found in other β,β'-dihydroxy carbonyl compounds like chrysazin, anthralin, 2,2'-dihydroxybenzophenone, and the dienol form of 1,3-dibenzoylacetone. But in these examples the two H-bonds are equivalent, while in the case of OHDBM they are chemically different, involving one enolic and one phenolic hydroxy group. OHDBM is thus an interesting model compound with two competing H-bonds to the same carbonyl group. In this communication we report some results of an IR spectroscopic and quantum theoretical investigation of the molecular and vibrational structure of OHDBM.
Original languageEnglish
Publication dateDec 2014
DOIs
Publication statusPublished - Dec 2014

Cite this

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title = "Intramolecular Hydrogen Bonding in (2-Hydroxybenzoyl)benzoylmethane Enol",
abstract = "In the stable enol tautomer of the title compound (OHDBM), one carbonyl group is flanked by two β-hydroxy groups, giving rise to bifold intramolecular H-bonding. A similar situation is found in other β,β'-dihydroxy carbonyl compounds like chrysazin, anthralin, 2,2'-dihydroxybenzophenone, and the dienol form of 1,3-dibenzoylacetone. But in these examples the two H-bonds are equivalent, while in the case of OHDBM they are chemically different, involving one enolic and one phenolic hydroxy group. OHDBM is thus an interesting model compound with two competing H-bonds to the same carbonyl group. In this communication we report some results of an IR spectroscopic and quantum theoretical investigation of the molecular and vibrational structure of OHDBM.",
author = "Hansen, {Bjarke Knud Vilster} and Morten Winther and Jens Spanget-Larsen",
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month = "12",
doi = "10.13140/2.1.2213.0243",
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Intramolecular Hydrogen Bonding in (2-Hydroxybenzoyl)benzoylmethane Enol. / Hansen, Bjarke Knud Vilster; Winther, Morten; Spanget-Larsen, Jens.

2014, .

Research output: Other contributionNet publication - Internet publicationResearch

TY - ICOMM

T1 - Intramolecular Hydrogen Bonding in (2-Hydroxybenzoyl)benzoylmethane Enol

AU - Hansen, Bjarke Knud Vilster

AU - Winther, Morten

AU - Spanget-Larsen, Jens

PY - 2014/12

Y1 - 2014/12

N2 - In the stable enol tautomer of the title compound (OHDBM), one carbonyl group is flanked by two β-hydroxy groups, giving rise to bifold intramolecular H-bonding. A similar situation is found in other β,β'-dihydroxy carbonyl compounds like chrysazin, anthralin, 2,2'-dihydroxybenzophenone, and the dienol form of 1,3-dibenzoylacetone. But in these examples the two H-bonds are equivalent, while in the case of OHDBM they are chemically different, involving one enolic and one phenolic hydroxy group. OHDBM is thus an interesting model compound with two competing H-bonds to the same carbonyl group. In this communication we report some results of an IR spectroscopic and quantum theoretical investigation of the molecular and vibrational structure of OHDBM.

AB - In the stable enol tautomer of the title compound (OHDBM), one carbonyl group is flanked by two β-hydroxy groups, giving rise to bifold intramolecular H-bonding. A similar situation is found in other β,β'-dihydroxy carbonyl compounds like chrysazin, anthralin, 2,2'-dihydroxybenzophenone, and the dienol form of 1,3-dibenzoylacetone. But in these examples the two H-bonds are equivalent, while in the case of OHDBM they are chemically different, involving one enolic and one phenolic hydroxy group. OHDBM is thus an interesting model compound with two competing H-bonds to the same carbonyl group. In this communication we report some results of an IR spectroscopic and quantum theoretical investigation of the molecular and vibrational structure of OHDBM.

U2 - 10.13140/2.1.2213.0243

DO - 10.13140/2.1.2213.0243

M3 - Net publication - Internet publication

ER -