Photooxidation of Aniline Derivatives Can Be Activated by
Freezing Their Aqueous Solutions

J 2017

Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions

CORROCHANO DÍAZ, Pablo, Dana NACHTIGALLOVÁ and Petr KLÁN

Basic information

Original name

Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions

Authors

CORROCHANO DÍAZ, Pablo (724 Spain, belonging to the institution), Dana NACHTIGALLOVÁ (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

ENVIRONMENTAL SCIENCE AND TECHNOLOGY, WASHINGTON, AMER CHEMICAL SOC, 2017, 0013-936X

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

20700 2.7 Environmental engineering

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 6.653

RIV identification code

RIV/00216224:14310/17:00095495

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.est.7b04510

UT WoS

000417549500026

Keywords in English

AIR-ICE INTERFACE; EXPERIMENTAL-COMPUTATIONAL APPROACH; DISSOLVED ORGANIC-MATTER; HABER-WEISS CYCLE; HYDROGEN-PEROXIDE; SPECTROSCOPIC PROPERTIES; ISOTOPE FRACTIONATION; PHOTOEXCITED ANILINE; HYDRATED ELECTRONS; SELF-ASSOCIATION

Abstract

V originále

A combined experimental and computational approach was, used to investigate the spectroscopic properties of three different aniline derivatives (aniline, N,N-dimethylaniline, and N,N-diethylaniline) in aqueous solutions and at the air-ice interface in the temperature range of 243-298 K The absorption and diffuse reflectance spectra of ice samples prepared by different techniques, such as slow or shock freezing of the aqueous solutions or vapor deposition on ice grains, exhibited unequivocal bathochromic shifts of 10-15 nm of the absorption maxima of anilines in frozen samples compared to those in liquid aqueous solutions. DFT and SCS-ADC(2) calculations showed that contaminant contaminant and contaminant-ice interactions are responsible for these shifts. Finally, we demonstrate that irradiation of anilines in the presence of a hydrogen peroxide/O-2 system by wavelengths that overlap only with the red-shifted absorption tails of anilines in frozen samples (while having a marginal overlap with their spectra in liquid solutions) can almost exclusively trigger a photochemical oxidation process. Mechanistic and environmental considerations are discussed.

Links

GA15-12386S, research and development project

Name: Dynamika a (foto)chemie polutantů na rozhraních led/vzduch a voda/vzduch z experimentu i teorie

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

CORROCHANO DÍAZ, Pablo, Dana NACHTIGALLOVÁ and Petr KLÁN. Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions. ENVIRONMENTAL SCIENCE AND TECHNOLOGY. WASHINGTON: AMER CHEMICAL SOC, 2017, vol. 51, No 23, p. 13763-13770. ISSN 0013-936X. Available from: https://dx.doi.org/10.1021/acs.est.7b04510.

@article{1407990,
   author = {Corrochano Díaz, Pablo and Nachtigallová, Dana and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {23},
   doi = {http://dx.doi.org/10.1021/acs.est.7b04510},
   keywords = {AIR-ICE INTERFACE; EXPERIMENTAL-COMPUTATIONAL APPROACH; DISSOLVED ORGANIC-MATTER; HABER-WEISS CYCLE; HYDROGEN-PEROXIDE; SPECTROSCOPIC PROPERTIES; ISOTOPE FRACTIONATION; PHOTOEXCITED ANILINE; HYDRATED ELECTRONS; SELF-ASSOCIATION},
   language = {eng},
   issn = {0013-936X},
   journal = {ENVIRONMENTAL SCIENCE AND TECHNOLOGY},
   title = {Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions},
   url = {https://pubs.acs.org/doi/10.1021/acs.est.7b04510},
   volume = {51},
   year = {2017}
}

TY  - JOUR
ID  - 1407990
AU  - Corrochano Díaz, Pablo - Nachtigallová, Dana - Klán, Petr
PY  - 2017
TI  - Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions
JF  - ENVIRONMENTAL SCIENCE AND TECHNOLOGY
VL  - 51
IS  - 23
SP  - 13763-13770
EP  - 13763-13770
PB  - AMER CHEMICAL SOC
SN  - 0013936X
KW  - AIR-ICE INTERFACE
KW  - EXPERIMENTAL-COMPUTATIONAL APPROACH
KW  - DISSOLVED ORGANIC-MATTER
KW  - HABER-WEISS CYCLE
KW  - HYDROGEN-PEROXIDE
KW  - SPECTROSCOPIC PROPERTIES
KW  - ISOTOPE FRACTIONATION
KW  - PHOTOEXCITED ANILINE
KW  - HYDRATED ELECTRONS
KW  - SELF-ASSOCIATION
UR  - https://pubs.acs.org/doi/10.1021/acs.est.7b04510
L2  - https://pubs.acs.org/doi/10.1021/acs.est.7b04510
N2  - A combined experimental and computational approach was, used to investigate the spectroscopic properties of three different aniline derivatives (aniline, N,N-dimethylaniline, and N,N-diethylaniline) in aqueous solutions and at the air-ice interface in the temperature range of 243-298 K The absorption and diffuse reflectance spectra of ice samples prepared by different techniques, such as slow or shock freezing of the aqueous solutions or vapor deposition on ice grains, exhibited unequivocal bathochromic shifts of 10-15 nm of the absorption maxima of anilines in frozen samples compared to those in liquid aqueous solutions. DFT and SCS-ADC(2) calculations showed that contaminant contaminant and contaminant-ice interactions are responsible for these shifts. Finally, we demonstrate that irradiation of anilines in the presence of a hydrogen peroxide/O-2 system by wavelengths that overlap only with the red-shifted absorption tails of anilines in frozen samples (while having a marginal overlap with their spectra in liquid solutions) can almost exclusively trigger a photochemical oxidation process. Mechanistic and environmental considerations are discussed.
ER  -

CORROCHANO DÍAZ, Pablo, Dana NACHTIGALLOVÁ and Petr KLÁN. Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions. \textit{ENVIRONMENTAL SCIENCE AND TECHNOLOGY}. WASHINGTON: AMER CHEMICAL SOC, 2017, vol.~51, No~23, p.~13763-13770. ISSN~0013-936X. Available from: https://dx.doi.org/10.1021/acs.est.7b04510.

Detailed Information on Publication Record