Hydrogen bonding mercaptans

No hydrogen bonding Hydrocarbons, carbon disulfide, mercaptans, solvents not included in above groups... 

Mercaptans R-S-H -S-H (2600-2500) (w) Only significant frequency around that region lowering of 50-150 cnr1 due to hydrogen bonding... 

Class V All other liquids—i.e., liquids having no hydrogen-bonding capabilities—e.g.. hydrocarbons, CSi, sulfides, mercaptans, halohydrocarbons not in class IV, nonmetallic elements such as iodine, phosphorus, sulfur. 

Marstokk, K.-M., and Mollendal, H., Microwave spectrum, conformational equilibrium, intramolecular hydrogen bonding and ab initio calculations for 2-furanmethanethiol (furfuryl mercaptan), Acta Chem. Scand., 48, 298-305 (1994). 

Studies on the inactivation of benzylpenicillin have shown that this substance has a strong preference for acylating j8-aminomercaptans, much less affinity for other amines, and none for other mercaptans. The product [e.g. 13.6) from j8-mercaptoethylamine] is acylated on the amino-group. The function of the mercapto-groups seems to be to form a hydrogen bond with the oxygen atom of the lactam and hence increase the polarization of the C=0 bond in the penicillin. 

Dimethyl sulfoxide is a very polar, high dipole moment, strong hydrogen bond accepting solvent It is has a high viscosity nearly equal to that of IPA. Typical impurities from the manufacturing process include dimethyl sulfide (from whidi DMSO is commonly manufactured) and dimethyl sulfone. Decomposition products include dimethyl sulfide, dimethyl sulfone, methyl mercaptan, and bis(methylthio> methane [1552]. 

By incorporating into the stationary phase a chiral charge transfer reagent also capable of hydrogen bonding, such as 2,2,2-trifluoro-l-[(10-methyl)-9-anthryl] ethanol, Pirkle and coworkers [18] have resolved substances which either contain a CT complexing moiety in their molecule, e.g. aromatic sulphoxides and lactones, or possess a function through which such a moiety can be introduced, e.g. alcohols, mercaptans, amines, amino alcohols, amino acids, hydroxy acids and esters. 

R. Benesch One has to assume complex formation because otherwise you wouldn t break the hydrogen bonds. But why in the case of, shall we say, the simple mercaptan, etc., do you get no effect Why don t you get an effect with other com-... 

The SH stretch in mercaptans and thiophenols absorbs at 2590-2540 The band is weak in the infrared but strong in the Raman spectra. Thiol acids C(=0)SH absorb in the same region and show only small hydrogen bonding shifts. The PSSH group absorbs broadly at 2480-2300 cm"Mn the bonded condensed state and sharply at 2590-2550 cm in dilute solu-tion. - ... 

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