The structures of seven gas phase identity S(N)2 reactions of the form CH3X + X- have been characterized with seven distinct theoretical methods: RHF, B3LYP, BLYP, BP86, MP2, CCSD, and CCSD(T), in conjunction with basis sets of double and triple zeta quality. Additionally, the energetics of said reactions have been definitively computed using focal point analyses utilizing extrapolation to the one-particle limit for the Hartree-Fock and MP2 energies using basis sets of up to aug-cc-pV5Z quality, inclusion of higher order correlation effects (CCSD and CCSD(T)] with basis sets of aug-cc-pVTZ quality, and additional auxiliary terms for core correlation and scalar relativistic effects. Final net activation barriers for the reactions are E-F,F(b) = -0.8, E-Cl,Cl(b) = 1.6, E-CN,CN(b) = 28.7, E-OH,OH(b) = 14.3, E-SH,SH(b) = 13.8, E-NH2,Nh2(b) =28.6, E-PH2,PH2(b) = 25.7 kcal mol(-1). General trends in the energetics, specifically the performance of the density functionals, and the component energies of the focal point analyses are discussed. The utility of classic Marcus theory as a technique for barrier predictions has been carefully analyzed. The standard Marcus theory results show disparities of up to 9 kcal mol(-1) with respect to explicitly computed results. However, when alternative approaches to Marcus theory, independent of the well-depths, are considered, excellent performance is achieved, with the largest deviations being under 3 kcal mol(-1).