Gas-phase acidities of CH2=C=X (X = CHI2 NH, O, and S) and barriers for the identity proton transfers (X=C=CH2 + HC dropC-X- reversible arrow X--C drop CH + CH2=C=X) as well as geometries and charge distributions of CH2=C=X, HC dropC-X- and the transition states of the proton transfer were determined by ab initio methods at the MP2/6-311 + G(d,p)//MP2/6-311+G(d,p) and B3LYP/6-311+G(d,p) levels of theory. The acidities were also calculated at the CCSD(T)/6-311+G(2df,p) level. A major objective of this study was to examine how the enhanced unsaturation of CH2=C=X compared to that of CH3CH=X may affect acidities, transition state imbalances, and intrinsic barriers of the identity proton transfer. The results show that the acidities are all higher while the barriers are lower than for the corresponding CH3CH=X series. The transition states are all imbalanced but less so than for the reactions of CH3CH=X.