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10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines : Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges. / Pozharskii, Alexander F.; Ozeryanskii, Valery A.; Mikshiev, Vladimir Y.; Antonov, Alexander S.; Chernyshev, Anatoly V.; Metelitsa, Anatoly V.; Borodkin, Gennady S.; Fedik, Nikita S.; Dyablo, Olga V.

в: Journal of Organic Chemistry, Том 81, № 13, 01.07.2016, стр. 5574-5587.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Pozharskii, AF, Ozeryanskii, VA, Mikshiev, VY, Antonov, AS, Chernyshev, AV, Metelitsa, AV, Borodkin, GS, Fedik, NS & Dyablo, OV 2016, '10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges', Journal of Organic Chemistry, Том. 81, № 13, стр. 5574-5587. https://doi.org/10.1021/acs.joc.6b00917

APA

Pozharskii, A. F., Ozeryanskii, V. A., Mikshiev, V. Y., Antonov, A. S., Chernyshev, A. V., Metelitsa, A. V., Borodkin, G. S., Fedik, N. S., & Dyablo, O. V. (2016). 10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges. Journal of Organic Chemistry, 81(13), 5574-5587. https://doi.org/10.1021/acs.joc.6b00917

Vancouver

Pozharskii AF, Ozeryanskii VA, Mikshiev VY, Antonov AS, Chernyshev AV, Metelitsa AV и пр. 10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges. Journal of Organic Chemistry. 2016 Июль 1;81(13):5574-5587. https://doi.org/10.1021/acs.joc.6b00917

Author

Pozharskii, Alexander F. ; Ozeryanskii, Valery A. ; Mikshiev, Vladimir Y. ; Antonov, Alexander S. ; Chernyshev, Anatoly V. ; Metelitsa, Anatoly V. ; Borodkin, Gennady S. ; Fedik, Nikita S. ; Dyablo, Olga V. / 10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines : Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges. в: Journal of Organic Chemistry. 2016 ; Том 81, № 13. стр. 5574-5587.

BibTeX

@article{4da554704c4f4d548266a5223c947f67,
title = "10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges",
abstract = "For the first time, 10-dimethylamino derivatives of benzo[h]quinoline 6 and benzo[h]quinazoline 7a-e as mixed analogues of archetypal 1,8-bis(dimethylamino)naphthalene ({"}proton sponge{"}) 1 and quino[7,8-h]quinoline 2a have been examined. Similar to 1 and 2, compounds 6 and 7 display rather high basicity, forming chelated monocations. At the same time, unexpected specifics of the protonated NMe2/ - N= systems consist of a strong shift of the NH proton to the 10-NMe2 group, contrary to the {"}aniline-pyridine{"} basicity rule. In case of 4H+, a rapid migration (in the NMR time scale) of the NH proton between two nitrogen atoms along the N-H···N hydrogen bond was registered at room temperature and frozen below -30 °C with the proton fixed on the NMe2 group. Two different approaches for classification of strong neutral nitrogen organic bases as proton sponges (kinetically inert compounds) or pseudo-proton sponges (kinetically active) are discussed. On this basis, benzoquinoline 6 was identified as staying closer to pseudo-proton sponges while 7a-e to proton sponges due to the presence in their molecules of bulky substituents in the pyrimidine ring. Other remarkable peculiarities of 6 and 7 are their yellow color and luminescence in the visible region distinguishing them from colorless 1 and 2a.",
author = "Pozharskii, {Alexander F.} and Ozeryanskii, {Valery A.} and Mikshiev, {Vladimir Y.} and Antonov, {Alexander S.} and Chernyshev, {Anatoly V.} and Metelitsa, {Anatoly V.} and Borodkin, {Gennady S.} and Fedik, {Nikita S.} and Dyablo, {Olga V.}",
year = "2016",
month = jul,
day = "1",
doi = "10.1021/acs.joc.6b00917",
language = "English",
volume = "81",
pages = "5574--5587",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "13",

}

RIS

TY - JOUR

T1 - 10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines

T2 - Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N= Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges

AU - Pozharskii, Alexander F.

AU - Ozeryanskii, Valery A.

AU - Mikshiev, Vladimir Y.

AU - Antonov, Alexander S.

AU - Chernyshev, Anatoly V.

AU - Metelitsa, Anatoly V.

AU - Borodkin, Gennady S.

AU - Fedik, Nikita S.

AU - Dyablo, Olga V.

PY - 2016/7/1

Y1 - 2016/7/1

N2 - For the first time, 10-dimethylamino derivatives of benzo[h]quinoline 6 and benzo[h]quinazoline 7a-e as mixed analogues of archetypal 1,8-bis(dimethylamino)naphthalene ("proton sponge") 1 and quino[7,8-h]quinoline 2a have been examined. Similar to 1 and 2, compounds 6 and 7 display rather high basicity, forming chelated monocations. At the same time, unexpected specifics of the protonated NMe2/ - N= systems consist of a strong shift of the NH proton to the 10-NMe2 group, contrary to the "aniline-pyridine" basicity rule. In case of 4H+, a rapid migration (in the NMR time scale) of the NH proton between two nitrogen atoms along the N-H···N hydrogen bond was registered at room temperature and frozen below -30 °C with the proton fixed on the NMe2 group. Two different approaches for classification of strong neutral nitrogen organic bases as proton sponges (kinetically inert compounds) or pseudo-proton sponges (kinetically active) are discussed. On this basis, benzoquinoline 6 was identified as staying closer to pseudo-proton sponges while 7a-e to proton sponges due to the presence in their molecules of bulky substituents in the pyrimidine ring. Other remarkable peculiarities of 6 and 7 are their yellow color and luminescence in the visible region distinguishing them from colorless 1 and 2a.

AB - For the first time, 10-dimethylamino derivatives of benzo[h]quinoline 6 and benzo[h]quinazoline 7a-e as mixed analogues of archetypal 1,8-bis(dimethylamino)naphthalene ("proton sponge") 1 and quino[7,8-h]quinoline 2a have been examined. Similar to 1 and 2, compounds 6 and 7 display rather high basicity, forming chelated monocations. At the same time, unexpected specifics of the protonated NMe2/ - N= systems consist of a strong shift of the NH proton to the 10-NMe2 group, contrary to the "aniline-pyridine" basicity rule. In case of 4H+, a rapid migration (in the NMR time scale) of the NH proton between two nitrogen atoms along the N-H···N hydrogen bond was registered at room temperature and frozen below -30 °C with the proton fixed on the NMe2 group. Two different approaches for classification of strong neutral nitrogen organic bases as proton sponges (kinetically inert compounds) or pseudo-proton sponges (kinetically active) are discussed. On this basis, benzoquinoline 6 was identified as staying closer to pseudo-proton sponges while 7a-e to proton sponges due to the presence in their molecules of bulky substituents in the pyrimidine ring. Other remarkable peculiarities of 6 and 7 are their yellow color and luminescence in the visible region distinguishing them from colorless 1 and 2a.

UR - http://www.scopus.com/inward/record.url?scp=84977531593&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b00917

DO - 10.1021/acs.joc.6b00917

M3 - Article

AN - SCOPUS:84977531593

VL - 81

SP - 5574

EP - 5587

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 13

ER -

ID: 41270642