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The molecular and crystal structures of N- para -toluenesulphonyl-N-methyl- α -aminoisobutyric acyl imidazole ( 1 ), and 3-(N- para -toluenesulphonyl- α -aminoisobutyric acyl)-1,3-thiazolidine-2-thione ( 2 ) have been determined by X-ray diffraction. Crystal parameters: ( 1 ) orthorhombic, space group  P 2 1 2 1 2 1 ,  a  = 11.735(2) Å,  b  = 19.990(3) Å,  c  = 6.925(1) Å, and  Z  = 4; ( 2 ) orthorhombic, space group  Pnc 2,  a  = 9.507(2) Å,  b  = 16.902(2) Å,  c  = 10.347(2) Å, and  Z  = 4. The structures were solved by direct methods. The least-squares refinements led to conventional  R  factors of 0.036 and 0.031 for ( 1 ) and ( 2 ), respectively. This is the first geometrical and conformational characterization at atomic resolution of N  α  -protected  α -aminoacids containing the elusive acyl imidazole and 3-acyl-1,3-thiazolidine-2-thione C-activating groups. Only the reactive carboxylic amide of ( 2 ) deviates significantly from planarity.

Reactive intermediates in peptide synthesis. Molecular and crystal structures of reactive carboxylic amides