imine Chem.
(ˈɪmiːn)
[ad. G. imin (A. Ladenburg 1883, in Ber. d. Deut. Chem. Ges. XVI. 1150), formed by altering amin amine (cf. imide, amide).]
Any compound containing the group {b2}NH (or the substituted form {b2}NR) attached to one carbon atom that forms part of a non-acidic organic group, or containing it in symmetrical compounds of the type R·NH·R; also applied (unsystematically) to other compounds in which it is attached to two carbon atoms (strictly, atoms forming part of non-acidic groups), esp. when they are part of a ring (as in ethylene imine, (CH2)2NH).
| 1883 Jrnl. Chem. Soc. XLIV. 910 (heading) Imines. 1889 G. M'Gowan tr. A. Bernthsen's Text-bk. Org. Chem. 194 If two hydrogen atoms in a molecule of ammonia are replaced by a divalent alcohol radicle, ‘Imines’, e.g. ethylene imine, (C2H4)NH{pp}, result. 1909 Proc. Chem. Soc. XXV. 309 Some confusion exists owing to the present system of nomenclature adopted for the imino-compounds. These substances, which possess the group C:NH, are obviously just as different from the secondary amines having the group C{btl1}C{bbl1} as the ketones with the group C:O are different from the ethers with the group C{btl1}C{bbl1}, yet the general name of imine is applied to both these classes. 1935 Jrnl. Amer. Chem. Soc. LVII. 2328/1 (heading) The preparation of ethylene imine from mono⁓ethanolamine. 1950 N. V. Sidgwick Chem. Elements I. 666 Imines of the type C{btl1}C{bbl1}C{b2}N·H rarely occur and are always unstable. 1967 I. L. Finar Org. Chem. (ed. 5) I. viii. 181 Aldehydes react with primary amines to form imines (Schiff bases)... R·CHO + R{p}NH2→R·CH{b2}NR{p} + H2O. 1970 Ambrose & Easty Cell Biol. viii. 267 The sugar molecules form imine linkages ({b2}NH) with the partially dissociated protein complexes. |