ISSN:
1572-8854
Keywords:
Ortho-heteroatoms interactions
;
chlorine-sulfur short contacts
;
quinolines
Source:
Springer Online Journal Archives 1860-2000
Topics:
Geosciences
,
Physics
Notes:
Abstract The crystal and molecular structures of two isomeric 3,4- and 4,3-chloro-(methylthio)quinolines have been determined. For 3-chloro-4-(methylthio)-quinoline (3-Cl−4-MeS−Q); triclinic, space group $$\bar P1$$ ,a=7.199(3),b=7.919(3),c=8.921(3) Å, α=89.74(3), β=74.29(3), γ=78.55(3)°. For 4-chloro-3-(methylthio)quinoline (4-Cl−3-MeS−Q): monoclinic, space group P21/n,a=12.860(4),b=5.424(2),c=13.434(4) Å, β=90.84(3)°. The values of the Cl...S distance as well as those for the Cl−C−C(S) and (Cl)C−C−S angles indicate the attractive interaction between ortho-situated heteroatoms in isomer 4-Cl−3-MeS−Q contrary to the effects observed in the case of 3-Cl−4-MeS−Q. The conclusions were confirmed by calculations of atomic charges withab initio method 4-31G basis set, which show positively charged sulfur atom in 4-Cl−3-MeS−Q and negatively charged sulfur in 3-Cl−4-MeS−Q.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01666101
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