1003-42-5Relevant articles and documents
Molecular and electronic structure of δ-valerothiolactone
Dugarte, Nahir Y.,Erben, Mauricio F.,Boese, Roland,Ge, Mao-Fa,Yao, Li,Della Vedova, Carlos O.
, p. 12540 - 12547 (2010)
The crystal structure of the six-member heterocyclic δ- valerothiolactone (1-thiocycloalkan-2-one) compound has been determined by X-ray diffraction at low temperature, revealing that its skeleton adopts a half-chair conformation. The conformation around the thioester group is almost planar with an anti orientation of the C=O double bond with respect the S-C single bond [C(2)-S(1)-C(6)-O(1) = 176.26(8)°]. The skeletal parameters, especially valence angles [∠-C5-C6-S = 121.19(6)°, ∠-O = C6-C5 = 122.25(8)°, ∠-C6-S-C2 = 106.80(4)°], differ from those typically found in acyclic thioester compounds, symptomatic of the presence of strain effects. The conventional ring strain energy was determined to be 7.5 kcal/mol at the MP2/6-311++G(d,p) level of calculation within the hyperhomodesmotic model approximation. Moreover, the valence electronic structure was investigated by HeI photoelectron spectroscopy assisted by quantum chemical calculations at the OVGF/6-311++G(d,p) level of theory. The first three bands at 9.35, 9.50, and 11.53 eV denote ionizations related with the nS, nO, and πC =O orbitals, respectively, demonstrating the importance of the -SC(O)- group in the outermost electronic properties.
Synthesis of thiolactones using benzyltriethylammonium tetrathiomolybdate as sulfur transfer reagent
Bhar, Debjani,Chandrasekaran
, p. 11835 - 11842 (2007/10/03)
An interesting sulfur transfer reaction mediated by benzyltiethylammonium tetrathiomolybdate [(PhCH2NEt3)2MoS4] converts ω-halo acid chlorides to the corresponding thiolactones in moderate to good yields in one
