Investigation of the reactivity of thiophene compounds towards butyllithium using the molecular electrostatic potential

被引：5

作者：

Blockhuys, F ^{[1
]}

Peten, C ^{[1
]}

Van Alsenoy, C ^{[1
]}

Geise, HJ ^{[1
]}

机构：

[1] Univ Instelling Antwerp, Dept Chem, B-2610 Wilrijk, Belgium

来源：

JOURNAL OF MOLECULAR STRUCTURE | 1998年 / 445卷 / 1-3期

关键词：

thiophene reactivity; butyllithium metallation conditions; molecular electrostatic potential;

D O I：

10.1016/S0022-2860(97)00424-9

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：

We calculated the total molecular electrostatic potential of six thiophene derivatives. This potential portrays the path of approach and coordination site of an electrophile. The calculations reproduce the known regioselectivity of BuLi mediated lithiation reactions and rationalize the low reactivity of BuLi towards 3,3'-dimethoxy-2,2'-bithienyl and lead to a better procedure to polymerize trans-1,2-bis(3-methoxy-2-thienyl)ethene. (C) 1998 Elsevier Science B.V.

引用

页码：187 / 195

页数：9

共 50 条

[31] Relation between the Molecular Electrostatic Potential and activity of some FF-MAS related sterol compounds
Boer, DR
Kooijman, H
van der Louw, J
Groen, M
Kelder, J
Kroon, J
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (10) : 2653 - 2659
[32] Analysis of electrostatic and hydrophobic complementarities between trypsin and Cucurbita maxima trypsin inhibitor 1 using molecular electrostatic potential
J Molec Struct, 1 (39):
[33] Analysis of electrostatic and hydrophobic complementarities between trypsin and Cucurbita maxima trypsin inhibitor I using molecular electrostatic potential
Nakajima, H
Kikuchi, O
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1996, 365 (01): : 39 - 45
[34] Prediction of the aqueous solvation free energy of organic compounds by using autocorrelation of molecular electrostatic potential surface properties combined with response surface analysis
Michielan, Lisa
Bacilieri, Magdalena
Kaseda, Chosei
Moro, Stefano
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (10) : 5733 - 5742
[35] On the Analysis of High Harmonic Generation Spectra of Atoms and Molecules Using Molecular Electrostatic Potential
Bag, Sampad
Chandra, Sankhabrata
Chakraborty, Souvick
Bhattacharya, Atanu
JOURNAL OF PHYSICAL CHEMISTRY A, 2021, 125 (17): : 3689 - 3695
[36] Predicting the Enthalpies of Sublimation of Cyclic Urea Derivatives Using a Model of the Molecular Electrostatic Potential
O. N. Ryzhova
O. V. Dorofeeva
Russian Journal of Physical Chemistry A, 2019, 93 : 1896 - 1901
[37] Generation of OPLS-like charges from molecular electrostatic potential using restraints
Henchman, RH
Essex, JW
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1999, 20 (05) : 483 - 498
[38] Explaining reaction mechanisms using the dual descriptor: a complementary tool to the molecular electrostatic potential
Jorge Ignacio Martínez-Araya
Journal of Molecular Modeling, 2013, 19 : 2715 - 2722
[39] Explaining reaction mechanisms using the dual descriptor: a complementary tool to the molecular electrostatic potential
Martinez-Araya, Jorge Ignacio
JOURNAL OF MOLECULAR MODELING, 2013, 19 (07) : 2715 - 2722
[40] Predicting the Enthalpies of Sublimation of Cyclic Urea Derivatives Using a Model of the Molecular Electrostatic Potential
Ryzhova, O. N.
Dorofeeva, O. V.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2019, 93 (10) : 1896 - 1901

← 1 2 3 4 5 →