The stabilization of thiepin by substitution

B.A. Hess, Jr; L.J. Schaad; David Reinhoudt

doi:10.1016/0040-4020(77)80289-5

The stabilization of thiepin by substitution

B.A. Hess, Jr, L.J. Schaad, David Reinhoudt

University of Twente

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Abstract

Resonance energies of 430 substituted thiepins have been calculated using a simple Hückel method described before. The results predict that thiepins substituted with electron-withdrawing groups (methoxycarbonyl and fluorine) will be less antiaromatic than the parent thiepin. Thus the calculated REPE of the only known type of monocyclic thiepin viz. 3,4 - bis(methoxycarbonyl) - 5 pyrrolidinothiepin (-0.007β) is less negative than that of the parent thiepin.

Original language	Undefined
Pages (from-to)	2683-2685
Journal	Tetrahedron
Volume	33
Issue number	20
DOIs	https://doi.org/10.1016/0040-4020(77)80289-5
Publication status	Published - 1977

Keywords

IR-68372

Access to Document

10.1016/0040-4020(77)80289-5

Hess77stabilization

Cite this

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title = "The stabilization of thiepin by substitution",

abstract = "Resonance energies of 430 substituted thiepins have been calculated using a simple H{\"u}ckel method described before. The results predict that thiepins substituted with electron-withdrawing groups (methoxycarbonyl and fluorine) will be less antiaromatic than the parent thiepin. Thus the calculated REPE of the only known type of monocyclic thiepin viz. 3,4 - bis(methoxycarbonyl) - 5 pyrrolidinothiepin (-0.007β) is less negative than that of the parent thiepin.",

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T1 - The stabilization of thiepin by substitution

AU - Hess, Jr, B.A.

AU - Schaad, L.J.

AU - Reinhoudt, David

PY - 1977

Y1 - 1977

N2 - Resonance energies of 430 substituted thiepins have been calculated using a simple Hückel method described before. The results predict that thiepins substituted with electron-withdrawing groups (methoxycarbonyl and fluorine) will be less antiaromatic than the parent thiepin. Thus the calculated REPE of the only known type of monocyclic thiepin viz. 3,4 - bis(methoxycarbonyl) - 5 pyrrolidinothiepin (-0.007β) is less negative than that of the parent thiepin.

AB - Resonance energies of 430 substituted thiepins have been calculated using a simple Hückel method described before. The results predict that thiepins substituted with electron-withdrawing groups (methoxycarbonyl and fluorine) will be less antiaromatic than the parent thiepin. Thus the calculated REPE of the only known type of monocyclic thiepin viz. 3,4 - bis(methoxycarbonyl) - 5 pyrrolidinothiepin (-0.007β) is less negative than that of the parent thiepin.

KW - IR-68372

U2 - 10.1016/0040-4020(77)80289-5

DO - 10.1016/0040-4020(77)80289-5

M3 - Article

SN - 0040-4020

VL - 33

SP - 2683

EP - 2685

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -