BETA-DIKETONE INTERACTIONS .12. THE STRUCTURE AND PROPERTIES OF 3-(3',4',5'-TRIMETHYLPHENYL)-PENTANE-2,4-DIONE, C14H18O2 - THE HYDROGEN-BOND ENERGY OF THE ENOL TAUTOMERS OF BETA-DIKETONES

被引：37

作者：

EMSLEY, J

MA, LYY

NYBURG, SC

PARKINS, AW

机构：

[1] Department of Chemistry, King's College, Strand, London

来源：

JOURNAL OF MOLECULAR STRUCTURE | 1990年 / 240卷

关键词：

D O I：

10.1016/0022-2860(90)80496-7

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The X-ray crystal structure of 3-(3′,4′,5′-trimethylphenyl) pentane-2,4-dione shows it to be the enol tautomer, with a hydrogen bond length RO&...o of 2.460 Å, and the enol ring remarkably symmetrical indicating a strong hydrogen bond. The hydrogen-bond energy is estimated to be 110±10 kJ mol-1, a value derived from the infra-red spectrum. In CDCl3 solutin 8% of the keto tautomer is present. © 1990.

引用

页码：59 / 67

页数：9

共 26 条

[1] Spectroscopic studies of the hydrogen bond. II. The shift of the O-H vibrational frequency in the formation of the hydrogen bond
Badger, RM
Bauer, SH
[J]. JOURNAL OF CHEMICAL PHYSICS, 1937, 5 (11) : 839 - 851
[2] THE INFRA-RED ABSORPTION BANDS ASSOCIATED WITH THE CHELATE RING IN SOME UNSATURATED HYDROXYCARBONYL COMPOUNDS
BRATOZ, S
HADZI, D
ROSSMY, G
[J]. TRANSACTIONS OF THE FARADAY SOCIETY, 1956, 52 (04): : 464 - 470
[3] MOLECULAR-STRUCTURE OF ACETYLACETONE - A CRYSTALLOGRAPHIC DETERMINATION
CAMERMAN, A
MASTROPAOLO, D
CAMERMAN, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) : 1584 - 1586
[4] CRYSTAL STRUCTURE OF 3,4,5-TRIMETHYLBENZOIC ACID
CANO, FH
MARTINEZ.S
GARCIABL.S
[J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1970, B 26 : 972 - &
[5] PROTONATION OF A BETA-DIKETONE - AN INTRAMOLECULAR HYDROGEN-BOND WITH AN EXTREMELY DESHIELDED PROTON
CLARK, DR
EMSLEY, J
HIBBERT, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (18) : 1252 - 1253
[6] BETA-DIKETONE INTERACTIONS .5. SOLVENT EFFECTS ON THE KETO-REVERSIBLE-ENOL EQUILIBRIUM
EMSLEY, J
FREEMAN, NJ
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1987, 161 : 193 - 204
[7] BETA-DIKETONE INTERACTIONS .2. PENTANE-2,4-DIONE AND TERTIARY-AMINES - INFRARED, NUCLEAR-MAGNETIC-RESONANCE, AND ABINITIO INVESTIGATIONS
EMSLEY, J
FREEMAN, NJ
PARKER, RJ
OVERILL, RE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (09): : 1479 - 1484
[8] BETA-DIKETONE INTERACTIONS .8. THE HYDROGEN-BONDING OF THE ENOL TAUTOMERS OF SOME 3-SUBSTITUTED PENTANE-2,4-DIONES
EMSLEY, J
MA, LYY
BATES, PA
MOTEVALLI, M
HURSTHOUSE, MB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (05): : 527 - 533
[9] BETA-DIKETONE INTERACTIONS .6. X-RAY MOLECULAR-STRUCTURE OF 3-(4-METHOXYPHENYL)PENTANE-2,4-DIONE, A BETA-DIKETONE ENOL TAUTOMER WITH A VERY STRONG HYDROGEN-BOND
EMSLEY, J
FREEMAN, NJ
BATES, PA
HURSTHOUSE, MB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02): : 297 - 299
[10] BETA-DIKETONE INTERACTIONS .7. X-RAY MOLECULAR-STRUCTURE OF 3-(4'-BIPHENYL)PENTANE-2,4-DIONE REVEALS AN ENOL TAUTOMER WITH A VERY STRONG HYDROGEN-BOND
EMSLEY, J
MA, LYY
BATES, PA
HURSTHOUSE, MB
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1988, 178 : 297 - 303

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