Ultrafast irreversible phototautomerization of o-nitrobenzaldehyde.

نویسندگان

  • Annapaola Migani
  • Verónica Leyva
  • Ferran Feixas
  • Thomas Schmierer
  • Peter Gilch
  • Inés Corral
  • Leticia González
  • Lluís Blancafort
چکیده

o-Nitrobenzaldehyde is photolabile because of an irreversible phototautomerization, whereas comparable aromatic compounds function as photoprotectors because the tautomerization is reversible. In this experimental and theoretical study we track down the cause of this difference to the electronic changes that occur during the tautomerization.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Irreversible phototautomerization of o-phthalaldehyde through electronic relocation.

The potential energy surface for the intramolecular excited state hydrogen transfer (IESHT) in ortho-phthalaldehyde (OPA), which generates an enol ketene, has been studied with ab initio calculations (MS-CASPT2//CASSCF). The goal of our study is to establish the mechanistic factors that make the primary phototautomerization step irreversible. Similar to what we recently described for ortho-nitr...

متن کامل

A non-adiabatic quantum-classical dynamics study of the intramolecular excited state hydrogen transfer in ortho-nitrobenzaldehyde.

Ab initio surface-hopping dynamics calculations have been performed to simulate the intramolecular excited state hydrogen transfer dynamics of ortho-nitrobenzaldehyde (o-NBA) in the gas phase from the electronic S(1) excited state. Upon UV excitation, the hydrogen is transferred from the aldehyde substituent to the nitro group, generating o-nitrosobenzoic acid through a ketene intermediate. The...

متن کامل

Four nitrobenzaldehyde isonicotinoylhydrazones at 120 K: four different supramolecular structures in two and three dimensions.

The molecules of 2-nitrobenzaldehyde isonicotinoylhydrazone, C13H10N4O3, (I), are linked into a three-dimensional framework by a combination of one N-H...N and three C-H...O hydrogen bonds. In the isomeric compound 3-nitrobenzaldehyde isonicotinoylhydrazone, (II), the molecules are linked into complex sheets by a combination of three hydrogen bonds, one each of the N-H...N, C-H...N and C-H...O ...

متن کامل

Hydrogen-bonded dimers in 2-nitrobenzaldehyde hydrazone and a three-dimensional hydrogen-bonded framework in 3-nitrobenzaldehyde hydrazone.

Molecules of 2-nitrobenzaldehyde hydrazone, C7H7N3O2, where Z' = 2, are linked by two N-H...N hydrogen bonds into isolated dimers, whereas in the isomeric 3-nitrobenzaldehyde hydrazone, where Z' = 1, the molecules are linked by one N-H...O hydrogen bond and one N-H...N hydrogen bond into a three-dimensional framework structure.

متن کامل

A consistent picture of the proton release mechanism of oNBA in water by ultrafast spectroscopy and ab initio molecular dynamics.

With a combination of transient pump-probe IR spectroscopy and ab initio molecular dynamics, the controversial pico- and nanosecond steps of the o-nitrobenzaldehyde (oNBA) photoreaction have been investigated in aqueous solution. In this way, the measured reaction kinetics have been complemented with an atomistic picture of the reactive events as obtained with unbiased simulations in explicit s...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 47 22  شماره 

صفحات  -

تاریخ انتشار 2011