In this paper we report the deprotonation yields, the pKa, and decay kinetics of the aci-nitro intermediates of some substituted 2-nitrobenzaldehydes that can be used as photoactivatable caged proton compounds. The decay of the aci-nitro absorbance for 2-nitrobenzaldehyde occurs within a few nanoseconds from photoexcitation. Addition of electron donating methoxy substituents at positions 4 and 5 leads to lower deprotonation yields, higher pKa, and slower decays of the aci-nitro intermediates. On the contrary, the decay rate is accelerated by the introduction of an electron-withdrawing Cl atom at position 4 in the phenyl ring, with little influence on the deprotonation yield and pKa of the aci-nitro intermediate.

Deprotonation yields, pKa, and aci-nitro decay rates in some substituted o-nitrobenzaldehydes / Abbruzzetti, Stefania; Carcelli, Mauro; Rogolino, Dominga; Viappiani, Cristiano. - In: PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. - ISSN 1474-905X. - 2:(2003), pp. 796-800. [10.1039/b301818k]

Deprotonation yields, pKa, and aci-nitro decay rates in some substituted o-nitrobenzaldehydes

ABBRUZZETTI, Stefania;CARCELLI, Mauro;ROGOLINO, Dominga;VIAPPIANI, Cristiano
2003

Abstract

In this paper we report the deprotonation yields, the pKa, and decay kinetics of the aci-nitro intermediates of some substituted 2-nitrobenzaldehydes that can be used as photoactivatable caged proton compounds. The decay of the aci-nitro absorbance for 2-nitrobenzaldehyde occurs within a few nanoseconds from photoexcitation. Addition of electron donating methoxy substituents at positions 4 and 5 leads to lower deprotonation yields, higher pKa, and slower decays of the aci-nitro intermediates. On the contrary, the decay rate is accelerated by the introduction of an electron-withdrawing Cl atom at position 4 in the phenyl ring, with little influence on the deprotonation yield and pKa of the aci-nitro intermediate.
Deprotonation yields, pKa, and aci-nitro decay rates in some substituted o-nitrobenzaldehydes / Abbruzzetti, Stefania; Carcelli, Mauro; Rogolino, Dominga; Viappiani, Cristiano. - In: PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. - ISSN 1474-905X. - 2:(2003), pp. 796-800. [10.1039/b301818k]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2298520
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