In:
Chemistry – A European Journal, Wiley, Vol. 29, No. 43 ( 2023-08)
Kurzfassung:
1,1’,10,10’‐Biphenothiazine and its S , S , S ’, S ’‐tetroxide are diaza[5]helicenes with N−N linkages. Kinetic experiments on racemization together with DFT calculations revealed that they undergo inversion through the N−N bond breaking pathway rather than the general conformational pathway. In these diaza[5] helicenes with this inversion mechanism, the reduction of electronic repulsion in the N−N bond by modification of S to SO 2 at the outer position of the helix led to a significantly higher inversion barrier, 35.3 kcal/mol, compared to [5]helicene. 1,1’,10,10’‐Biphenothiazine S , S , S ’, S ’‐tetroxide was highly resistant to acid‐mediated N−N bond breaking and racemization under acidic conditions.
Materialart:
Online-Ressource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.202301466
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2023
ZDB Id:
1478547-X
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