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. Author manuscript; available in PMC: 2019 Jan 8.
Published in final edited form as: Org Biomol Chem. 2015 Nov 26;14(3):920–939. doi: 10.1039/c5ob01692d

Table 6.

Optimized geometries and selected parameters of (S)-aziridinium ions 3a′, 5a′, 6a′, and 7a′ and transition states (TS) for formation of (R)-β-halo amines 3a, 5a, 6a, and 7a from ring opening reaction of aziridinium ion (Az+) with halide via a SN2 pathway (PBE0/cc-pVTZ).

graphic file with name nihms-1004224-t0012.jpg
parameter (S)-3a′
(X =F)		 (S)-3a-TS
(X = F)		 (S)-5a′
(X = Cl)		 (S)-5a-TS
(X = Cl)		 (S)-6a′
(X = Br)		 (S)-6a-TS
(X = Br)		 (S)-7a′
(X = I)		 (S)-7a-TS
(X = I)
X-C2* 2.610 2.184 3.184 2.705 3.351 2.846 3.591 3.068
X-C3* 3.228 2.931 3.434 3.086 3.564 3.217 3.779 3.445
N-C2* 1.527 1.813 1.517 1.693 1.516 1.715 1.515 1.749
N-C3* 1.487 1.474 1.494 1.485 1.494 1.482 1.494 1.477
C2-C3* 1.473 1.460 1.469 1.453 1.469 1.454 1.469 1.457
X# −0.75 −0.68 −0.82 −0.82 −0.82 −0.80 −0.84 −0.79
N# −0.38 −0.46 −0.38 −0.43 −0.38 −0.43 −0.38 −0.43
C2# −0.06 −0.05 −0.04 0.00 −0.04 0.00 −0.03 0.00
C3# −0.21 −0.23 −0.20 −0.21 −0.20 −0.22 −0.20 −0.22
*

All bond lengths are in Angstrom.

#

Atomic charges are calculated within the NPA framework.