Supplementary Material for Perkin Transactions 2

This journal is © The Royal Society of Chemistry 2002

Supplementary data

Möbius and Hückel Spiro-aromatic Systems

Möbius and Hückel Spiroaromatic Systems

Henry S. Rzepa* and Kieron Taylor

Department of Chemistry, Imperial College, London, SW7 2AY

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Table 1. Crystal structures obtained from the Cambridge Database

Dioxaphosphepine examples
BIQTAW HATHIT HEKPES
Dioxaphosphepine examples
JOWFAC LODHOB OXPCTP10
Diazaphosphepine example
WEMTAJ
Dioxaphosphole and Diazaphosphole example
DOFSUM YUJFOV
Triarsenoazobenzene example
HPTARZ
Calculated energies (hartree) and NICS values (ppm) for 5–10
Substituents Energy NICSa Substituents Energy NICSa
5, X = O, R = H −1493.59245 1.0 (−2.2)/−0.4 5, X = NH, R = H −1453.84743
 1.9 (−1.8)/−0.3
5, X = O, R = benzo −1800.91060 1.5 (−1.7)/1.2
5, X = O, R = F −1890.49767b 0.9 (−2.3)/−5.0 5, X = NF, R = F −2049.05166
(2.8)c		 1.5 (−2.0)/−9.6
6, X = O, R = F −1237.02783b −7.9 (−7.7)/−5.9 6, X = N, R = F −1395.58808
(7.0)c		 −7.7(−7.6)/−11.6
6, X = S, R = F −1882.94836 −5.3 (−5.6)/−9.5
6, X = O, R = F, Asd −3129.40995 −7.6 (−8.0)/−7.8 6, X = NF, R = F, Asd −3287.97290 −7.3 (−7.8)/−12.2
7, X = O, R = F −1614.62798
 0.3 (−2.8)/−7.8 7, X = NF, R = F
 −1773.19255
(5.2)e		 2.4/−9.2
8, X = O, R = F −961.16074
 −8.8 (−8.6)/−7.1 8, X = NF, R = F
 −1119.72821
(4.0)e		 −7.7 (−7.5)/−9.2
9, X = O, R = F −1494.32476
 −0.9 (0.2)/−4.5 9, X = NF, R = F
 −1652.88226
 0.4 (0.6)/−8.6
10, X = O, R = F, R' = H −1159.51846
 2.6/−4.8
 10, X = NF, R = F, R' = H
 −1318.07670
 5.2/−8.3
10, X = O, R = F, R' = F −1457.18499 −17.2/−4.6 10, X = NF, R = F, R' = F
 1615.74390
(1.3)f
 −16.2/−8.3

aNICS(0) value at ring B centroid (NICS(1) value 1 Å above ring B centroid)/NICS(0) value at ring A centroid. bGeometry optimisation converges to C2 symmetric conformation. cRelative energy (kcal mol−1) Cs symmetric conformation. dAs replacing P. eRelative energy (kcal mol−1) of anti-conformation, with no symmetry. fRelative energy (kcal mol−1) of chiral diastereoisomer.