Theoretical investigation of the relationship between proton NMR chemical shift and hydrogen bond strength

被引：90

作者：

Kumar, GA ^{[1
]}

McAllister, MA ^{[1
]}

机构：

[1] Univ N Texas, Dept Chem, Denton, TX 76203 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 20期

关键词：

D O I：

10.1021/jo980759h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hartree-Fock, Moller-Plesset, and DFT (BLYP, B3LYP) calculations have been carried out using the 6-31+G(d,p) basis set to study the relationship between calculated H-1 NMR chemical shifts and calculated hydrogen bond strengths in several model low-barrier hydrogen band complexes. For both the formic acid-substituted formate anion and enol-substituted enolate anion model systems, we find an excellent linear correlation between calculated hydrogen bond strength and predicted H-1 NMR chemical shift, with an average slope of 1.5 kcal/mol per ppm chemical shift.

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页码：6968 / 6972

页数：5

相关论文

共 67 条

[51] THE NONEXISTENCE OF SPECIALLY STABILIZED HYDROGEN-BONDS IN ENZYMES [J].

SCHEINER, S ;

KAR, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (26) :6970-6975

[52] Proton transfer properties of imidazole [J].

Scheiner, S ;

Yi, MY .

JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (22) :9235-9241

[53] A SIMPLE METHOD FOR DETERMINING THE RELATIVE STRENGTHS OF NORMAL AND LOW-BARRIER HYDROGEN-BONDS IN SOLUTION - IMPLICATIONS TO ENZYME CATALYSIS [J].

SCHWARTZ, B ;

DRUECKHAMMER, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :11902-11905

[54] The change in hydrogen bond strength accompanying charge rearrangement: Implications for enzymatic catalysis [J].

Shan, SO ;

Herschlag, D .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (25) :14474-14479

[55] The energetics of hydrogen bonds in model systems: Implications for enzymatic catalysis [J].

Shan, SO ;

Loh, S ;

Herschlag, D .

SCIENCE, 1996, 272 (5258) :97-101

[56] Characterization of low-barrier hydrogen bonds .7. Relationship between strength and geometry of short-strong hydrogen bonds. The formic acid formate anion model system. An ab initio and DFT investigation [J].

Smallwood, CJ ;

McAllister, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11277-11281

[57] Hydrogen deuterium isotope effects on the NMR chemical shifts and geometries of intermolecular low-barrier hydrogen-bonded complexes [J].

Smirnov, SN ;

Golubev, NS ;

Denisov, GS ;

Benedict, H ;

SchahMohammedi, P ;

Limbach, HH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4094-4101

[58] THE CRYSTAL STRUCTURES OF THE ACID SALTS OF SOME MONOBASIC ACIDS .1. POTASSIUM HYDROGEN BISPHENYLACETATE [J].

SPEAKMAN, JC .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (DEC) :3357-3365

[59]

Sule P, 1996, J CHEM PHYS, V104, P8524, DOI 10.1063/1.471601

[60] On the quantum nature of the shared proton in hydrogen bonds [J].

Tuckerman, ME ;

Marx, D ;

Klein, ML ;

Parrinello, M .

SCIENCE, 1997, 275 (5301) :817-820

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