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(a) The preferred directions of interaction of an electrophile and a nucleophile with respect to the disulfide plane. (An electrophile can also interact with the other lone-pair orbital.) (b) The incipient reaction of a nucleophile (the carbonyl group) with the disulfide group. (c) Schematic representation of the orbital interaction [nO→σ*(Sγ—Sγ′)] revealed by NBO calculations.
