Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity
Тип публикации: Journal Article
Дата публикации: 2013-07-17
scimago Q3
wos Q3
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SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Краткое описание
Novel 2-alkynyl-, 4-alkynyl-, and 2,7-dialkynyl derivatives of 1,8-bis(dimethylamino)naphthalene (‘proton sponge’) have been synthesized and their basicity values have been measured by competitive NMR studies in DMSO. These indicate that, while the para-alkynyl groups decrease the basicity of the parent proton sponge approximately by one order of magnitude in accordance with their electron-accepting nature, the influence of ortho-alkynyl functionalities is unexpectedly base-enhancing. The latter phenomenon has been ascribed to the appearance of a buttressing effect, but some other factors can be also at work.
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Filatova E. A. et al. Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity // Synlett. 2013. Vol. 24. No. 19. pp. 2515-2518.
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Filatova E. A., Pozharskii A. F., Gulevskaya A. V., Vistorobskii N., Ozeryanskii V. A. Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity // Synlett. 2013. Vol. 24. No. 19. pp. 2515-2518.
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TY - JOUR
DO - 10.1055/s-0033-1339339
UR - https://doi.org/10.1055/s-0033-1339339
TI - Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity
T2 - Synlett
AU - Filatova, Ekaterina A.
AU - Pozharskii, Alexander F.
AU - Gulevskaya, Anna V
AU - Vistorobskii, Nikolay
AU - Ozeryanskii, Valery A.
PY - 2013
DA - 2013/07/17
PB - Georg Thieme Verlag KG
SP - 2515-2518
IS - 19
VL - 24
SN - 0936-5214
SN - 1437-2096
ER -
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@article{2013_Filatova,
author = {Ekaterina A. Filatova and Alexander F. Pozharskii and Anna V Gulevskaya and Nikolay Vistorobskii and Valery A. Ozeryanskii},
title = {Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity},
journal = {Synlett},
year = {2013},
volume = {24},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-0033-1339339},
number = {19},
pages = {2515--2518},
doi = {10.1055/s-0033-1339339}
}
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MLA
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Filatova, Ekaterina A., et al. “Synthesis of 2-Alkynyl-, 4-Alkynyl-, and 2,7-Dialkynyl-1,8-bis(dimethylamino)naphthalenes and the Unexpected Influence of ortho-Alkynyl Groups on Their Basicity.” Synlett, vol. 24, no. 19, Jul. 2013, pp. 2515-2518. https://doi.org/10.1055/s-0033-1339339.