Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes

S M Aucott, H L Milton, S D Robertson, A M Z Slawin, J D Woollins

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. 

LanguageEnglish
Pages530-542
Number of pages13
JournalHeteroatom Chemistry
Volume15
Issue number7
DOIs
Publication statusPublished - 2004

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Naphthalenes
Molecular modeling
Crystal structure
Bond length
Sulfur
Oxides
Molecular structure
Atoms
Oxidation
naphthalene

Keywords

  • proton sponge
  • salts
  • analog
  • molecular modeling
  • naphthalenes

Cite this

Aucott, S M ; Milton, H L ; Robertson, S D ; Slawin, A M Z ; Woollins, J D . / Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes. In: Heteroatom Chemistry. 2004 ; Vol. 15, No. 7. pp. 530-542.
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abstract = "The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. ",
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Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes. / Aucott, S M ; Milton, H L ; Robertson, S D ; Slawin, A M Z ; Woollins, J D .

In: Heteroatom Chemistry, Vol. 15, No. 7, 2004, p. 530-542.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Crystal structures and molecular modeling of 1,8 chalcogenide-substituted naphthalenes

AU - Aucott, S M

AU - Milton, H L

AU - Robertson, S D

AU - Slawin, A M Z

AU - Woollins, J D

PY - 2004

Y1 - 2004

N2 - The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. 

AB - The molecular structures of naphtho[1,8-cd][1,2]dithiole, naphtho[1,8-cd][1,2]diselenole, naphtho[1,8-cd][1,2]ditellurole, naphtho[1,8-cd][1,2]dithiole I-oxide, naphtho[1,8-cd][1,2]dithiole 1,1-dioxide, and naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxideand naphtho[1,8-cd][1,2]dithiole 1,1,2,2-tetroxide are compared. The E-E distance varies, broadly reflecting the degree of distortion imposed by the rigid naphthalene backbone as well as the degree of oxidation at sulfur. The naphthalene backbone imposes shortening of E-E bond lengths when E = S and Se compared to Ph-E-E-Ph systems but is itself subject to distortion as a consequence of the steric bulk of the E atoms. 

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KW - salts

KW - analog

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