Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring

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Standard

Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring. / Drazenovic, Josip; Rozic, Tomislav; Doslic, Nada; Basaric, Nikola.

I: Journal of Organic Chemistry, Bind 87, Nr. 14, 2022, s. 9148-9156.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Drazenovic, J, Rozic, T, Doslic, N & Basaric, N 2022, 'Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring', Journal of Organic Chemistry, bind 87, nr. 14, s. 9148-9156. https://doi.org/10.1021/acs.joc.2c00818

APA

Drazenovic, J., Rozic, T., Doslic, N., & Basaric, N. (2022). Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring. Journal of Organic Chemistry, 87(14), 9148-9156. https://doi.org/10.1021/acs.joc.2c00818

Vancouver

Drazenovic J, Rozic T, Doslic N, Basaric N. Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring. Journal of Organic Chemistry. 2022;87(14):9148-9156. https://doi.org/10.1021/acs.joc.2c00818

Author

Drazenovic, Josip ; Rozic, Tomislav ; Doslic, Nada ; Basaric, Nikola. / Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring. I: Journal of Organic Chemistry. 2022 ; Bind 87, Nr. 14. s. 9148-9156.

Bibtex

@article{b2966dce840a4679bd3abcd076982b6c,
title = "Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring",
abstract = "ABSTRACT: Excited state intramolecular proton transfer (ESIPT) has been documented from an amino NH2 group to a carbon atom of an adjacent aromatic ring. This finding changes the paradigm, as hitherto such processes have not been considered as plausible due to slow protonation of carbon and low (photo)acidity of the NH2 group. The ESIPT was studied by irradiation of 2-(2-aminophenyl)naphthalene in CH3CN???D2O, whereupon regiospecific incorporation of deuterium takes place at the naphthalene position 1, with a quantum yield of ?? = 0.11. A synergy of experimental and computational investigations completely unraveled the mechanism of this important photochemical reaction. Upon excitation to the photoreactive S2(La) state, a favorable redistribution of charge sets the stage for ESIPT to the carbon atom in naphthalene position 1. H2O molecules are needed, as they increase the excitation energy and oscillator strength for the population of the S2(La) state. The gain in energy is used to surmount a small energy barrier on the pathway from the Franck???Condon geometry to the conical intersection with the S0, delivering azaquinone methide.",
keywords = "INTRAMOLECULAR PROTON-TRANSFER, TRANSFER ESIPT, POLARIZATION PROPAGATOR, CARBON-ATOMS, PHENOL OH, WATER, PHOTOADDITION, PHOTOPHYSICS, TRYPTOPHAN, DYNAMICS",
author = "Josip Drazenovic and Tomislav Rozic and Nada Doslic and Nikola Basaric",
year = "2022",
doi = "10.1021/acs.joc.2c00818",
language = "English",
volume = "87",
pages = "9148--9156",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "14",

}

RIS

TY - JOUR

T1 - Excited State Intramolecular Proton Transfer (ESIPT) from -NH2 to the Carbon Atom of a Naphthyl Ring

AU - Drazenovic, Josip

AU - Rozic, Tomislav

AU - Doslic, Nada

AU - Basaric, Nikola

PY - 2022

Y1 - 2022

N2 - ABSTRACT: Excited state intramolecular proton transfer (ESIPT) has been documented from an amino NH2 group to a carbon atom of an adjacent aromatic ring. This finding changes the paradigm, as hitherto such processes have not been considered as plausible due to slow protonation of carbon and low (photo)acidity of the NH2 group. The ESIPT was studied by irradiation of 2-(2-aminophenyl)naphthalene in CH3CN???D2O, whereupon regiospecific incorporation of deuterium takes place at the naphthalene position 1, with a quantum yield of ?? = 0.11. A synergy of experimental and computational investigations completely unraveled the mechanism of this important photochemical reaction. Upon excitation to the photoreactive S2(La) state, a favorable redistribution of charge sets the stage for ESIPT to the carbon atom in naphthalene position 1. H2O molecules are needed, as they increase the excitation energy and oscillator strength for the population of the S2(La) state. The gain in energy is used to surmount a small energy barrier on the pathway from the Franck???Condon geometry to the conical intersection with the S0, delivering azaquinone methide.

AB - ABSTRACT: Excited state intramolecular proton transfer (ESIPT) has been documented from an amino NH2 group to a carbon atom of an adjacent aromatic ring. This finding changes the paradigm, as hitherto such processes have not been considered as plausible due to slow protonation of carbon and low (photo)acidity of the NH2 group. The ESIPT was studied by irradiation of 2-(2-aminophenyl)naphthalene in CH3CN???D2O, whereupon regiospecific incorporation of deuterium takes place at the naphthalene position 1, with a quantum yield of ?? = 0.11. A synergy of experimental and computational investigations completely unraveled the mechanism of this important photochemical reaction. Upon excitation to the photoreactive S2(La) state, a favorable redistribution of charge sets the stage for ESIPT to the carbon atom in naphthalene position 1. H2O molecules are needed, as they increase the excitation energy and oscillator strength for the population of the S2(La) state. The gain in energy is used to surmount a small energy barrier on the pathway from the Franck???Condon geometry to the conical intersection with the S0, delivering azaquinone methide.

KW - INTRAMOLECULAR PROTON-TRANSFER

KW - TRANSFER ESIPT

KW - POLARIZATION PROPAGATOR

KW - CARBON-ATOMS

KW - PHENOL OH

KW - WATER

KW - PHOTOADDITION

KW - PHOTOPHYSICS

KW - TRYPTOPHAN

KW - DYNAMICS

U2 - 10.1021/acs.joc.2c00818

DO - 10.1021/acs.joc.2c00818

M3 - Journal article

C2 - 35763664

VL - 87

SP - 9148

EP - 9156

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -

ID: 314436681