Transannular sulfur-nitrogen interaction in 1,5-thiazonine derivatives: an X-ray study

M. Kuti, J. Rábai, I. Kapovits, A. Kucsman, L. Párkányí, G. Argay, A. Kálmán

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A sulfoxide-lactam (2) and sulfide-N-acetyllactam (3), each with a nine-membered, boat-like 1,5-thiazonine ring, have been prepared and their molecular structures determined by X-ray diffraction. Only compound 2, with a trans-amide structure, exhibits sulfur-nitrogen close contact with a sulfurane-like trigonal bipyramidal geometry about sulfur (r(S⋯N) = 2.780(1)Å; θ(OS⋯N) = 171.0(1)°). The interatomic distances r(SO) = 1.501(1) Å and r(OS⋯N) = 4.281(1) Å are in agreement with the usual SO double bond and S⋯N close contact rather than with OSN hypervalent bonds. Owing to the bulky N-acetyl group, the amide part in the ring of compound 3 has a cis structure with sulfur and nitrogen atoms lying 4.045(2) Å apart.

Original languageEnglish
Pages (from-to)161-169
Number of pages9
JournalJournal of Molecular Structure
Volume318
Issue numberC
DOIs
Publication statusPublished - Mar 3 1994

Fingerprint

Sulfur
sulfoxide
Nitrogen
sulfur
X-Rays
Derivatives
Amides
nitrogen
X rays
amides
Lactams
x rays
Ships
rings
boats
Boats
interactions
Sulfides
Molecular Structure
X-Ray Diffraction

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

Transannular sulfur-nitrogen interaction in 1,5-thiazonine derivatives : an X-ray study. / Kuti, M.; Rábai, J.; Kapovits, I.; Kucsman, A.; Párkányí, L.; Argay, G.; Kálmán, A.

In: Journal of Molecular Structure, Vol. 318, No. C, 03.03.1994, p. 161-169.

Research output: Contribution to journalArticle

@article{6477f3b94bb34dc29076dba666229c5b,
title = "Transannular sulfur-nitrogen interaction in 1,5-thiazonine derivatives: an X-ray study",
abstract = "A sulfoxide-lactam (2) and sulfide-N-acetyllactam (3), each with a nine-membered, boat-like 1,5-thiazonine ring, have been prepared and their molecular structures determined by X-ray diffraction. Only compound 2, with a trans-amide structure, exhibits sulfur-nitrogen close contact with a sulfurane-like trigonal bipyramidal geometry about sulfur (r(S⋯N) = 2.780(1){\AA}; θ(OS⋯N) = 171.0(1)°). The interatomic distances r(SO) = 1.501(1) {\AA} and r(OS⋯N) = 4.281(1) {\AA} are in agreement with the usual SO double bond and S⋯N close contact rather than with OSN hypervalent bonds. Owing to the bulky N-acetyl group, the amide part in the ring of compound 3 has a cis structure with sulfur and nitrogen atoms lying 4.045(2) {\AA} apart.",
author = "M. Kuti and J. R{\'a}bai and I. Kapovits and A. Kucsman and L. P{\'a}rk{\'a}ny{\'i} and G. Argay and A. K{\'a}lm{\'a}n",
year = "1994",
month = "3",
day = "3",
doi = "10.1016/0022-2860(93)07890-9",
language = "English",
volume = "318",
pages = "161--169",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "C",

}

TY - JOUR

T1 - Transannular sulfur-nitrogen interaction in 1,5-thiazonine derivatives

T2 - an X-ray study

AU - Kuti, M.

AU - Rábai, J.

AU - Kapovits, I.

AU - Kucsman, A.

AU - Párkányí, L.

AU - Argay, G.

AU - Kálmán, A.

PY - 1994/3/3

Y1 - 1994/3/3

N2 - A sulfoxide-lactam (2) and sulfide-N-acetyllactam (3), each with a nine-membered, boat-like 1,5-thiazonine ring, have been prepared and their molecular structures determined by X-ray diffraction. Only compound 2, with a trans-amide structure, exhibits sulfur-nitrogen close contact with a sulfurane-like trigonal bipyramidal geometry about sulfur (r(S⋯N) = 2.780(1)Å; θ(OS⋯N) = 171.0(1)°). The interatomic distances r(SO) = 1.501(1) Å and r(OS⋯N) = 4.281(1) Å are in agreement with the usual SO double bond and S⋯N close contact rather than with OSN hypervalent bonds. Owing to the bulky N-acetyl group, the amide part in the ring of compound 3 has a cis structure with sulfur and nitrogen atoms lying 4.045(2) Å apart.

AB - A sulfoxide-lactam (2) and sulfide-N-acetyllactam (3), each with a nine-membered, boat-like 1,5-thiazonine ring, have been prepared and their molecular structures determined by X-ray diffraction. Only compound 2, with a trans-amide structure, exhibits sulfur-nitrogen close contact with a sulfurane-like trigonal bipyramidal geometry about sulfur (r(S⋯N) = 2.780(1)Å; θ(OS⋯N) = 171.0(1)°). The interatomic distances r(SO) = 1.501(1) Å and r(OS⋯N) = 4.281(1) Å are in agreement with the usual SO double bond and S⋯N close contact rather than with OSN hypervalent bonds. Owing to the bulky N-acetyl group, the amide part in the ring of compound 3 has a cis structure with sulfur and nitrogen atoms lying 4.045(2) Å apart.

UR - http://www.scopus.com/inward/record.url?scp=0011790864&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0011790864&partnerID=8YFLogxK

U2 - 10.1016/0022-2860(93)07890-9

DO - 10.1016/0022-2860(93)07890-9

M3 - Article

AN - SCOPUS:0011790864

VL - 318

SP - 161

EP - 169

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - C

ER -