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The photochemistry and crystal structures of four monothioimides have been studied: N-phenyl-3-phenyl-N-[phenyl(thiocarbonyl)]propanamide, C22H19NOS, (1a); N-(4-bromophenyl)-N-[phenyl(thiocarbonyl)]-3-phenyl-propanamide, C22H18BrNOS, (1b); N-(4-bromo-2,6-dimethylphenyl)-3-phenyl-N-[phenyl(thiocarbonyl)]propanamide, C24H22BrNOS, (1c); and N-[4-methoxyphenyl(thiocarbonyl)]-N-phenyl-3-phenylpropanamide, C23H21NO2S, (1d). All four molecules adopt similar (ES,ZO) conformations, which are not suitable for photochemical γ-hydrogen abstraction; short intramolecular O...C(S) contacts (2.8 Å) suggest a new mechanism with nucleophilic attack by the carbonyl O atom on the C=S double bond; the presence of water is also essential for the reaction to proceed.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks tonyc5, 1a, 1b, 1c, 1d

hkl

Structure factor file (CIF format)
Contains datablock 1a

hkl

Structure factor file (CIF format)
Contains datablock 1b

hkl

Structure factor file (CIF format)
Contains datablock 1c

hkl

Structure factor file (CIF format)
Contains datablock 1d

CCDC references: 129774; 129775; 129776; 129777

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