The stabilization of thiepin by substitution

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

Research output: Contribution to journalArticleAcademic

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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 languageUndefined
Pages (from-to)2683-2685
JournalTetrahedron
Volume33
Issue number20
DOIs
Publication statusPublished - 1977

Keywords

  • IR-68372

Cite this

Hess, Jr, B.A. ; Schaad, L.J. ; Reinhoudt, David. / The stabilization of thiepin by substitution. In: Tetrahedron. 1977 ; Vol. 33, No. 20. pp. 2683-2685.
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The stabilization of thiepin by substitution. / Hess, Jr, B.A.; Schaad, L.J.; Reinhoudt, David.

In: Tetrahedron, Vol. 33, No. 20, 1977, p. 2683-2685.

Research output: Contribution to journalArticleAcademic

TY - JOUR

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

VL - 33

SP - 2683

EP - 2685

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -