The use of density functional theory-based reactivity descriptors in molecular similarity calculations

被引：36

作者：

Boon, G ^{[1
]}

De Proft, F ^{[1
]}

Langenaeker, W ^{[1
]}

Geerlings, P ^{[1
]}

机构：

[1] Free Univ Brussels, Fak Wetenschappen, Eenheid Algemene Chem, B-1050 Brussels, Belgium

来源：

CHEMICAL PHYSICS LETTERS | 1998年 / 295卷 / 1-2期

关键词：

D O I：

10.1016/S0009-2614(98)00936-1

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：

Molecular similarity is studied via density functional theory-based similarity indices using a numerical integration method. Complementary to the existing similarity indices, we introduce a reactivity-related similarity index based on the local softness. After a study of some test systems, a series of peptide isosteres is studied in view of their importance in pharmacology. The whole of the present work illustrates the importance of the study of molecular similarity based on both shape and reactivity. (C) 1998 Elsevier Science B.V. All rights reserved.

引用

页码：122 / 128

页数：7

共 32 条

[1] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[2] MOLECULAR SCF CALCULATIONS FOR GROUND STATE OF SOME 3-MEMBERED RING MOLECULES - (CH2)3, (CH2)2NH, (CH2)2NH2+, (CH2)2O, (CH2)2S, (CH)2CH2, AND N2CH2 [J].

BONACCOR.R ;

SCROCCO, E ;

TOMASI, J .

JOURNAL OF CHEMICAL PHYSICS, 1970, 52 (10) :5270-&

[3] ABINITIO COMPUTATION OF MOLECULAR SIMILARITY [J].

BOWENJENKINS, PE ;

COOPER, DL ;

RICHARDS, WG .

JOURNAL OF PHYSICAL CHEMISTRY, 1985, 89 (11) :2195-2197

[4] HOW SIMILAR IS A MOLECULE TO ANOTHER - AN ELECTRON-DENSITY MEASURE OF SIMILARITY BETWEEN 2 MOLECULAR-STRUCTURES [J].

CARBO, R ;

LEYDA, L ;

ARNAU, M .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1980, 17 (06) :1185-1189

[5] Local softness as a regioselectivity indicator in [4+2] cycloaddition reactions [J].

Damoun, S ;

VandeWoude, G ;

Mendez, F ;

Geerlings, P .

JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (05) :886-893

[6] Contribution of the shape factor sigma(r) to atomic and molecular electronegativities [J].

DeProft, F ;

Geerlings, P .

JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (29) :5344-5346

[7] Chemical potential, hardness, hardness and softness kernel and local hardness in the isomorphic ensemble of density functional theory [J].

DeProft, F ;

Liu, SB ;

Parr, RG .

JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3000-3006

[8]

DUGHAN L, 1991, J MOL STRUC-THEOCHEM, V81, P481, DOI 10.1016/0166-1280(91)85120-V

[9]

Geerlings P., 1998, ADV QUANTUM CHEM, V33, P303, DOI DOI 10.1016/S0065-3276(08)60442-6

[10]

Geerlings P., 1996, THEORET COMPUT CHEM, V4, P773

← 1 2 3 4 →