Boyd Group Electronegativity Influence on the Parr Global Electrophilicity of Vilsmeier Reagent-Derived Imidates: New Insights toward Improving Mitsunobu Chemistry

Author

Jeremy M. Carr
Gregory S. Tschumper, Missouri University of Science and TechnologyFollow
A. Paige Lathem

Abstract

Reactivities of 19 methylated imidate analogs were examined using B3LYP and M06-2X DFT methods. The resulting HOMO and LUMO energies of each optimized structure were used to calculate corresponding Parr global electrophilicity (ω) values. When the resulting quantities were compared against Boyd group electronegativity (X_G) values, a clear correlation was observed, suggesting that electron-withdrawing effects influence the reactivity of imidates. These findings represent an important first step in developing a novel method toward improving traditional Mitsunobu functionalization reactions.

Recommended Citation

J. M. Carr et al., "Boyd Group Electronegativity Influence on the Parr Global Electrophilicity of Vilsmeier Reagent-Derived Imidates: New Insights toward Improving Mitsunobu Chemistry," Helvetica Chimica Acta, vol. 98, no. 4, pp. 582 - 588, Wiley, Apr 2015.

The definitive version is available at https://doi.org/10.1002/hlca.201400340

Department(s)

Chemistry

Publication Status

Full Access

Keywords and Phrases

Boyd group electronegativity; Density-functional theory; Imidates; Mitsunobu chemistry; Parr global electrophilicity

International Standard Serial Number (ISSN)

1522-2675; 0018-019X

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 Wiley, All rights reserved.

Publication Date

01 Apr 2015