A computational characterization of boron-oxygen multiple bonding in HN=CH-CH=CH-NH-BO.

The Journal of Physical Chemistry. a
Joseph D LarkinCharles W Bock

Abstract

Structures, relative energies, and bonding characteristics for various conformers of 3-imino-N-(oxoboryl)prop-1-en-1-amine, HN=CH-CH=CH-NH-BO, and the corresponding borocycle (-HN=CH-CH=CH-NH-B-)O are discussed using results from second-order Møller-Plesset (MP2) perturbation theory with the Dunning-Woon correlation-consistent cc-pVDZ, aug-cc-pVDZ, and cc-pVTZ basis sets. These MP2 results are compared to those from computationally efficient density functional theory (DFT) calculations using the LDA, PBE, TPSS, BLYP, B3LYP, BVP86, OLYP, O3LYP, and PBE1PBE functionals in conjunction with the economical Pople-type 6-311++G(d,p) basis set to evaluate the suitability of these DFT/6-311++G(d,p) levels for use with larger boron-containing systems. The effects of an aqueous environment were incorporated into the calculations using COSMO methodology. The calculated boron-oxygen bond lengths, orbital compositions, and bond orders in all the (acyclic) HN=CH-CH=CH-NH-BO conformers were consistent with the presence of a boron-oxygen triple bond, similar to that found in H-BO and H2N-BO. The (-HN=CH-CH=CH-NH-B-)O borocycle is predicted to be planar (C2v symmetry), and it is approximately 30 kcal/mol lower in energy than any of the (acyclic)...Continue Reading

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Jun 28, 2007·The Journal of Physical Chemistry. a·Joseph D LarkinCharles W Bock
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Mar 1, 2007·Journal of Chemical Theory and Computation·Alpeshkumar K MaldeEvans C Coutinho

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Citations

Oct 9, 2013·Journal of Molecular Modeling·Sharity Morales-MezaMario Sanchez
Aug 5, 2011·The Journal of Organic Chemistry·Hari Prasad KokatlaMahesh K Lakshman
Sep 26, 2016·Journal of Molecular Modeling·Sharity Morales-MezaMario Sanchez
Sep 28, 2018·Current Medicinal Chemistry·Antonio Abad GarciaJose G Trujillo-Ferrara
Sep 17, 2020·International Journal of Molecular Sciences·Panchanan MaitiGary L Dunbar

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