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1,8-Bis(tetramethylguanidino)naphtalene (TMGN): a new superbasic and kinetically active „proton sponge

Raab, V. and Kipke, J. and Gschwind, R. M. and Sundermeyer, J. (2002) 1,8-Bis(tetramethylguanidino)naphtalene (TMGN): a new superbasic and kinetically active „proton sponge. Chemistry - A European Journal 8 (7), pp. 1682-1693.

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Abstract

1,8-Bis(tetramethylguanidino)naphthalene (TMGN, 1) is a new, readily accessible, and stable proton sponge with an experimental pKBH+ value of 25.1 in MeCN, which is nearly seven orders of magnitude higher in basicity than the classical proton sponge 1,8-bis(dimethylamino)-naphthalene (DMAN). Because of the sterically less crowded character of the proton-accepting sp2-nitrogen atoms, TMGN also has ...

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Item Type:Article
Date:2002
Institutions:Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind
Identification Number:
ValueType
10.1002/1521-3765(20020402)8:7<1682::AID-CHEM1682>3.0.CO;2-RDOI
Keywords:basicity; NMR spectroscopy; peralkylated guanidines; protonation; proton sponges
Subjects:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:No
Owner: Nikola Kastner-Pustet
Deposited On:11 Nov 2009 17:17
Last Modified:11 Nov 2009 17:17
Item ID:10644
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