Abstract
The structure of the local anaesthetic benzocaine was solved by direct methods and refined to anR of 0·12 for 531 observed reflections. The packing of the molecule is stabilised by N−H … O hydrogen-bonds (2–97 Â). The alkyl chain attached to the benzene ring is intrans-trans conformation. The benzoic moiety shows a quinonoid character as found in some other local anaesthetics.
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Beall R, Herdklotz J and Sass R L 1970Biochem. Biophys. Res. Commun. 39 324
Brown G M and Marsh R E 1963Acta Cryst. B16 191
Cesur A F and Richards J P G 1965Z. Kristallogr. 122 283
Domenicano A, Vaciago A and Coulson C A 1975Acta Cryst. B31 221
Gantzel P K, Sparks R A and Trueblood K N 1961 Program LALS, University of California, USA
Hughes E W 1941J. Am. Chem. Soc. 65 1737
International Tables for X-ray Crystallography 1962 (Birmingham: Kynoch Press) Vol. 3
Karle J 1968Acta Cryst. B24 182
Kahino S, Ishida M and Haisa M 1982Acta Cryst. B38 1868
Main P, Fiske S J, Hull S E, Lessinger L, Germain G, Declercq J P and Woolfson M M 1980 A system of computer programs for the automatic solution of crystal structures from X-ray diffraction data, University of York, UK
Pletcher J, Sax M and Yoo C S 1972Acta Cryst. B28 378
Sax M, Pletcher J and Gustaffson B 1970Acta Cryst. B26 114
Sax M, Pletcher J, Yoo C and Stewart J M 1971Acta Cryst. B27 1635
Shiono R 1968 Block diagonal least squares program for the IBM 1130 Department of Crystallography, University of Pittsburgh, USA
Sinha B K, Subramanian E, Vasantha Pattabhi and Trotter J 1984Indian J. Pure Appl. Phys. 22 249
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Sinha, B.K., Pattabhi, V. Crystal structure of benzocaine—A local anaesthetic. Proc. Indian Acad. Sci. (Chem. Sci.) 98, 229–234 (1987). https://doi.org/10.1007/BF02900724
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DOI: https://doi.org/10.1007/BF02900724