Intrinsic Relative Scales of Electrophilicity and Nucleophilicity

被引：23

作者：

Chamorro, Eduardo ^{[1
]}

Duque-Norena, Mario ^{[1
]}

Notario, Rafael ^{[2
]}

Perez, Patricia ^{[1
]}

机构：

[1] Univ Andres Bello, Fac Ciencias Exactas, Dept Ciencias Quim, Santiago, Chile

[2] CSIC, Inst Quim Fis Rocasolano, Madrid, Spain

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2013年 / 117卷 / 12期

关键词：

DENSITY-FUNCTIONAL THEORY; QUANTITATIVE CHARACTERIZATION; CHEMICAL-REACTIVITY; EXPERIMENTAL-MODELS; UNIVERSAL APPROACH; ORGANIC-MOLECULES; INDEX; CYCLOADDITION; POTENTIALS; PHILICITY;

D O I：

10.1021/jp312143t

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 formulation of the second-order perturbation approach to the stabilization energy of the A-B interacting species due to charge transfer is revisited. Intrinsic (i.e., electronic) theoretical indices for both relative electrophilicity and nucleophilicity are proposed for any electrophile (A)-nucleophile (B) pairs of combining species. By using the new descriptors, an electronic analogue to the Mayr-Patz linear free relationship has been successfully tested in the context of available experimental evidence reported for reactions of primary and secondary amines with benzhydrylium ions.

引用

页码：2636 / 2643

页数：8

共 50 条

[41] RELATIVE NUCLEOPHILICITY - THE ROLE OF SOLVATION AND THERMODYNAMICS
BACH, RD
WINTER, JE
MCDOUALL, JJW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) : 8586 - 8593
[42] Tuning the Nucleophilicity and Electrophilicity of Group 10 Elements through Substituent Effects: A DFT Study
Burguera, Sergi
Bauza, Antonio
Frontera, Antonio
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (21)
[43] MOLECULAR-ORBITAL STUDY ON THE NUCLEOPHILICITY AND THE ELECTROPHILICITY OF FREE-RADICALS IN ABSTRACTION REACTIONS
SHINOHARA, H
IMAMURA, A
MASUDA, T
KONDO, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (10) : 2801 - 2807
[44] Information-theoretic quantities as effective descriptors of electrophilicity and nucleophilicity in density functional theory
Fu, Jia
Li, Meng
Rong, Chunying
Zhao, Dongbo
Liu, Shubin
JOURNAL OF MOLECULAR MODELING, 2024, 30 (10)
[45] RELATIVE NUCLEOPHILICITY OF SOME MESOIONIC THIONES
TALUKDAR, PB
CHAKRABORTY, A
INDIAN JOURNAL OF CHEMISTRY, 1975, 13 (07): : 661 - 663
[46] A Relation between Different Scales of Electrophilicity: Are the Scales Consistent Along a Chemical Reaction?
Morell, Christophe
Herrera, Barbara
Gutierrez-Oliva, Soledad
Ceron, Maria-Luisa
Grand, Andre
Toro-Labbe, Alejandro
JOURNAL OF PHYSICAL CHEMISTRY A, 2012, 116 (26): : 7074 - 7081
[47] RELATIVE ELECTROPHILICITY OF IODINE ISOCYANATE DIBROMOCARBENE AND BROMINE
GEBELEIN, CG
SWERN, D
CHEMISTRY & INDUSTRY, 1965, (33) : 1462 - +
[48] Intrinsic acidity and electrophilicity of gaseous propargyl/allenyl carbocations
Lalli, Priscila M.
Corilo, Yuri E.
Abdelnur, Patricia V.
Eberlin, Marcos N.
Laali, Kenneth K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (11) : 2580 - 2585
[49] Atom-based machine learning for estimating nucleophilicity and electrophilicity with applications to retrosynthesis and chemical stability
Ree, Nicolai
Wollschlaeger, Jan M.
Goeller, Andreas H.
Jensen, Jan H.
CHEMICAL SCIENCE, 2025,
[50] Relationship between nucleophilicity/electrophilicity indices and reaction mechanisms for the nucleophilic substitution reactions of carbonyl compounds
Campodonico, P
Santos, JG
Andres, J
Contreras, R
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (04) : 273 - 281

← 1 2 3 4 5 →