Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings

D. Szabó, István Kapovits, Árpád Kucsman, M. Czugler, Vilmos Fülöp, A. Kálmán

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

1-[2′-(N-methylcarbamoyl)phenyl]-3H-2,1-naphto-(1,8-d,e)-oxathiin-1-ium chloride (2), 1-[2′-(N-methylcarbamoyl)-phenyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (3), 1-[8′-(N-methylcarbamoyl)naphtyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (4) and 1-(8′-carboxylatonaphtyl)-2-methyl-3-oxo-3H-1,2-naphto-(1,8-d,e)-thiazin-1-ium dipolar ion (5) cyclic sulfonium salts were prepared and their chemical properties investigated (spirosulfurane-formation, hydrolysis). The molecular structures obtained from x-ray diffraction can be described with a considerably distorted trigonal bipyramidal arrangement of the ligands about the sulfonium center, with O/N-S ... O=apical angles of 173.9, 164.9, 156.6, and 159.0°, as well as with S-O/N apical bond lengths of 1.648, 1.671, 1.664, and 1.682 Å. The structures exhibit relatively short S ... O close contacts with interatomic distances of 2.253, 2.448, 2.795, and 2.619 Å.

Original languageEnglish
Pages (from-to)529-535
Number of pages7
JournalStructural Chemistry
Volume2
Issue number5
DOIs
Publication statusPublished - Aug 1991

Fingerprint

Molecular Structure
Molecular structure
Chlorides
molecular structure
Salts
chlorides
salts
Oxathiins
rings
zwitterions
Bond length
interactions
chemical properties
Chemical properties
hydrolysis
Hydrolysis
x ray diffraction
Diffraction
X-Rays
Ions

ASJC Scopus subject areas

  • Chemistry(all)
  • Structural Biology

Cite this

Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings. / Szabó, D.; Kapovits, István; Kucsman, Árpád; Czugler, M.; Fülöp, Vilmos; Kálmán, A.

In: Structural Chemistry, Vol. 2, No. 5, 08.1991, p. 529-535.

Research output: Contribution to journalArticle

@article{0f9a968812be4491ab643488f7470ad8,
title = "Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings",
abstract = "1-[2′-(N-methylcarbamoyl)phenyl]-3H-2,1-naphto-(1,8-d,e)-oxathiin-1-ium chloride (2), 1-[2′-(N-methylcarbamoyl)-phenyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (3), 1-[8′-(N-methylcarbamoyl)naphtyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (4) and 1-(8′-carboxylatonaphtyl)-2-methyl-3-oxo-3H-1,2-naphto-(1,8-d,e)-thiazin-1-ium dipolar ion (5) cyclic sulfonium salts were prepared and their chemical properties investigated (spirosulfurane-formation, hydrolysis). The molecular structures obtained from x-ray diffraction can be described with a considerably distorted trigonal bipyramidal arrangement of the ligands about the sulfonium center, with O/N-S ... O=apical angles of 173.9, 164.9, 156.6, and 159.0°, as well as with S-O/N apical bond lengths of 1.648, 1.671, 1.664, and 1.682 {\AA}. The structures exhibit relatively short S ... O close contacts with interatomic distances of 2.253, 2.448, 2.795, and 2.619 {\AA}.",
author = "D. Szab{\'o} and Istv{\'a}n Kapovits and {\'A}rp{\'a}d Kucsman and M. Czugler and Vilmos F{\"u}l{\"o}p and A. K{\'a}lm{\'a}n",
year = "1991",
month = "8",
doi = "10.1007/BF00672886",
language = "English",
volume = "2",
pages = "529--535",
journal = "Structural Chemistry",
issn = "1040-0400",
publisher = "Springer New York",
number = "5",

}

TY - JOUR

T1 - Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings

AU - Szabó, D.

AU - Kapovits, István

AU - Kucsman, Árpád

AU - Czugler, M.

AU - Fülöp, Vilmos

AU - Kálmán, A.

PY - 1991/8

Y1 - 1991/8

N2 - 1-[2′-(N-methylcarbamoyl)phenyl]-3H-2,1-naphto-(1,8-d,e)-oxathiin-1-ium chloride (2), 1-[2′-(N-methylcarbamoyl)-phenyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (3), 1-[8′-(N-methylcarbamoyl)naphtyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (4) and 1-(8′-carboxylatonaphtyl)-2-methyl-3-oxo-3H-1,2-naphto-(1,8-d,e)-thiazin-1-ium dipolar ion (5) cyclic sulfonium salts were prepared and their chemical properties investigated (spirosulfurane-formation, hydrolysis). The molecular structures obtained from x-ray diffraction can be described with a considerably distorted trigonal bipyramidal arrangement of the ligands about the sulfonium center, with O/N-S ... O=apical angles of 173.9, 164.9, 156.6, and 159.0°, as well as with S-O/N apical bond lengths of 1.648, 1.671, 1.664, and 1.682 Å. The structures exhibit relatively short S ... O close contacts with interatomic distances of 2.253, 2.448, 2.795, and 2.619 Å.

AB - 1-[2′-(N-methylcarbamoyl)phenyl]-3H-2,1-naphto-(1,8-d,e)-oxathiin-1-ium chloride (2), 1-[2′-(N-methylcarbamoyl)-phenyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (3), 1-[8′-(N-methylcarbamoyl)naphtyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (4) and 1-(8′-carboxylatonaphtyl)-2-methyl-3-oxo-3H-1,2-naphto-(1,8-d,e)-thiazin-1-ium dipolar ion (5) cyclic sulfonium salts were prepared and their chemical properties investigated (spirosulfurane-formation, hydrolysis). The molecular structures obtained from x-ray diffraction can be described with a considerably distorted trigonal bipyramidal arrangement of the ligands about the sulfonium center, with O/N-S ... O=apical angles of 173.9, 164.9, 156.6, and 159.0°, as well as with S-O/N apical bond lengths of 1.648, 1.671, 1.664, and 1.682 Å. The structures exhibit relatively short S ... O close contacts with interatomic distances of 2.253, 2.448, 2.795, and 2.619 Å.

UR - http://www.scopus.com/inward/record.url?scp=0039860381&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0039860381&partnerID=8YFLogxK

U2 - 10.1007/BF00672886

DO - 10.1007/BF00672886

M3 - Article

VL - 2

SP - 529

EP - 535

JO - Structural Chemistry

JF - Structural Chemistry

SN - 1040-0400

IS - 5

ER -