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Shielding in and around Oxazole, Imidazole, and Thiazole: How Does the Second Heteroatom Affect Aromaticity and Bonding?

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Shielding in and around Oxazole, Imidazole, and Thiazole : How Does the Second Heteroatom Affect Aromaticity and Bonding? / Horner, Kate E.; Karadakov, Peter B.

In: Journal of Organic Chemistry, Vol. 80, No. 14, 17.07.2015, p. 7150-7157.

Research output: Contribution to journalArticle

Harvard

Horner, KE & Karadakov, PB 2015, 'Shielding in and around Oxazole, Imidazole, and Thiazole: How Does the Second Heteroatom Affect Aromaticity and Bonding?', Journal of Organic Chemistry, vol. 80, no. 14, pp. 7150-7157. https://doi.org/10.1021/acs.joc.5b01010

APA

Horner, K. E., & Karadakov, P. B. (2015). Shielding in and around Oxazole, Imidazole, and Thiazole: How Does the Second Heteroatom Affect Aromaticity and Bonding? Journal of Organic Chemistry, 80(14), 7150-7157. https://doi.org/10.1021/acs.joc.5b01010

Vancouver

Horner KE, Karadakov PB. Shielding in and around Oxazole, Imidazole, and Thiazole: How Does the Second Heteroatom Affect Aromaticity and Bonding? Journal of Organic Chemistry. 2015 Jul 17;80(14):7150-7157. https://doi.org/10.1021/acs.joc.5b01010

Author

Horner, Kate E. ; Karadakov, Peter B. / Shielding in and around Oxazole, Imidazole, and Thiazole : How Does the Second Heteroatom Affect Aromaticity and Bonding?. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 14. pp. 7150-7157.

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@article{8a45bdd785874de896a5e91989be1b3c,
title = "Shielding in and around Oxazole, Imidazole, and Thiazole: How Does the Second Heteroatom Affect Aromaticity and Bonding?",
abstract = "Isotropic magnetic shielding distributions in the regions of space surrounding oxazole, imidazole, and thiazole are used to investigate aromaticity and bonding in these five-membered heterocycles with two heteroatoms. This is achieved by constructing HF-GIAO and MP2-GIAO (Hartree-Fock and second-order M{\o}ller-Plesset perturbation theory with gauge-including atomic orbitals) isotropic shielding plots, within the 6-311++G(d,p) basis, using regular two-dimensional 0.05 {\AA} grids in the molecular plane and in planes 0.5 and 1 {\AA} above it. The extent of isotropic shielding delocalization in the contour plots in planes 1 {\AA} above the molecular plane, which is a new sensitive two-dimensional aromaticity criterion, indicates that aromaticity decreases in the order thiazole > imidazole > oxazole; in combination with previous results on furan, pyrrole, and thiophene (J. Org. Chem. 2013, 78, 8037-9043), the aromaticity ordering in the six five-membered heterocycles becomes thiophene > thiazole > pyrrole > imidazole > furan > oxazole. The results suggest that the inclusion of a second heteroatom in a five-membered heterocycle has a detrimental effect on its aromaticity, which is very minor in oxazole, when compared to furan, and small but noticeable in imidazole and pyrrole and in thiazole and thiophene.",
author = "Horner, {Kate E.} and Karadakov, {Peter B.}",
year = "2015",
month = "7",
day = "17",
doi = "10.1021/acs.joc.5b01010",
language = "English",
volume = "80",
pages = "7150--7157",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "14",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Shielding in and around Oxazole, Imidazole, and Thiazole

T2 - How Does the Second Heteroatom Affect Aromaticity and Bonding?

AU - Horner, Kate E.

AU - Karadakov, Peter B.

PY - 2015/7/17

Y1 - 2015/7/17

N2 - Isotropic magnetic shielding distributions in the regions of space surrounding oxazole, imidazole, and thiazole are used to investigate aromaticity and bonding in these five-membered heterocycles with two heteroatoms. This is achieved by constructing HF-GIAO and MP2-GIAO (Hartree-Fock and second-order Møller-Plesset perturbation theory with gauge-including atomic orbitals) isotropic shielding plots, within the 6-311++G(d,p) basis, using regular two-dimensional 0.05 Å grids in the molecular plane and in planes 0.5 and 1 Å above it. The extent of isotropic shielding delocalization in the contour plots in planes 1 Å above the molecular plane, which is a new sensitive two-dimensional aromaticity criterion, indicates that aromaticity decreases in the order thiazole > imidazole > oxazole; in combination with previous results on furan, pyrrole, and thiophene (J. Org. Chem. 2013, 78, 8037-9043), the aromaticity ordering in the six five-membered heterocycles becomes thiophene > thiazole > pyrrole > imidazole > furan > oxazole. The results suggest that the inclusion of a second heteroatom in a five-membered heterocycle has a detrimental effect on its aromaticity, which is very minor in oxazole, when compared to furan, and small but noticeable in imidazole and pyrrole and in thiazole and thiophene.

AB - Isotropic magnetic shielding distributions in the regions of space surrounding oxazole, imidazole, and thiazole are used to investigate aromaticity and bonding in these five-membered heterocycles with two heteroatoms. This is achieved by constructing HF-GIAO and MP2-GIAO (Hartree-Fock and second-order Møller-Plesset perturbation theory with gauge-including atomic orbitals) isotropic shielding plots, within the 6-311++G(d,p) basis, using regular two-dimensional 0.05 Å grids in the molecular plane and in planes 0.5 and 1 Å above it. The extent of isotropic shielding delocalization in the contour plots in planes 1 Å above the molecular plane, which is a new sensitive two-dimensional aromaticity criterion, indicates that aromaticity decreases in the order thiazole > imidazole > oxazole; in combination with previous results on furan, pyrrole, and thiophene (J. Org. Chem. 2013, 78, 8037-9043), the aromaticity ordering in the six five-membered heterocycles becomes thiophene > thiazole > pyrrole > imidazole > furan > oxazole. The results suggest that the inclusion of a second heteroatom in a five-membered heterocycle has a detrimental effect on its aromaticity, which is very minor in oxazole, when compared to furan, and small but noticeable in imidazole and pyrrole and in thiazole and thiophene.

UR - http://www.scopus.com/inward/record.url?scp=84937598692&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b01010

DO - 10.1021/acs.joc.5b01010

M3 - Article

VL - 80

SP - 7150

EP - 7157

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -