Synthesis and characterization of novel derivatives of N-(ferrocenesulfonyl)carbamic acid. X-ray structure determination of ferrocenesulfonamide and N-(ferrocenesulfonyl)- N′-butylurea

Abstract

Ferrocenesulfonamide, 1, was converted to novel N-(ferrocenesulfonyl)ureas and N-(ferrocenesulfonyl)carbamates via reacting 1 with the corresponding organic isocyanates or chloroformic acid esters. The molecular structures of 1 and N-(ferrocenesulfonyl)- N′-butylurea were determined by single-crystal X-ray diffraction. Crystal data: 1: monoclinic, P2 1/ c, with unit cell dimensions a=12.563(1), b=9.977(2), c=8.557(1) Å, and β=98.71(1)°, V=1060.2(3) Å 3, Z=4; 3e: orthorombic, Pbca, a=9.278(1), b=15.892(4), c=22.043(3) Å, and V=3250.2(10) Å 3, Z=8. In both 1 and 3e, the Fe–C distances of the substituted Cp ring follow a special sequence, the Fe–C(S) bonds being shorter than the Fe–C bonds with the neighboring or remote C atoms.