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. Author manuscript; available in PMC: 2014 Sep 11.
Published in final edited form as: Chem Rev. 2013 Aug 29;113(9):6949–6985. doi: 10.1021/cr400121w

Table 7.

Ionic products from gas-phase reactions of the para-benzyne anion with selected compounds. Reproduced with permission from reference 246. Reproduced with permission from reference 246. Copyright (1998) John Wiley & Sons, Ltd.

Compound para-Benzyne anion
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NH3 No reaction
ND3 C6H4-nDn−• (n = 1,2)
H2O No signal
D2O OD−,C6H4-nDn−• (n = 1,2)
CS2 C6H4S−•, C6H4S2−•
N2O C6H4O−•, (C5H4−•)
CH3SSCH3 CH3S−, CH3SCH2S−
NO2 NO2−
NO C6H4NO−, C6H4(NO)2−•
O2 C6H4O−•
RX, X = Cl, Br, R = alkyl X−
CH3OH CH3O−
CH3OCH3 No reaction
PhCH3 PhCH2−
Cyclohexa-1,3-diene c-C6H7−