Proton+sponge

=__**Proton Sponge**__ =

=
Proton Sponge is a compound that was first made in 1968 by Roger Alder FDS. He made it at the University of Bristol. The actual name for it is 1,8-Bis(dimethylamino)napthalene, however the name Proton Sponge was given to it by Sigma-Aldrich. The IUPAC name is N,N,N',N'-tetramethylnaphthalene-1,8-diamine. Another name it can go by is (DMAN).=====

**Essential Properties**
It has a pKmedia type="custom" key="4819539" of 12.1, making it one of the strongest amine bases known. It is highly basic because of the relief of strain upon protonation and/or the strong interaction between the nitrogen pairs. It is a weak nucleophile, which is one reason it is used in organic synthesis as a non-nucleophilic base. It absorbs the protons slowly, hence the sponge name. The molecular formula is Cmedia type="custom" key="4819565"Hmedia type="custom" key="4819573"Nmedia type="custom" key="4819585". The molar mass is 214.31g/mol. The melting point is 47.8°C. The boiling point is between 144 and 145°C. It is insoluble in water. It is found to be light sensitive. It is a pale brownish-pink crystalline powder.

__**//% Compositions//**__
By Number C = 41.18% H = 52.94% N = 5.82%

By Mass C = 78.46% H = 8.47% N = 13.07%

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Proton Sponge is used to absorb protons slowly, hence the name Proton Sponge. This is important in many reactions to view them in a sort of slower manner. When it absorbs the protons its structure changes. It then consists of a rigid aromatic framework, substituted by two amino groups that are connected by a powerful hydrogen bond bridge.(See below Picture)=====

http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-46DM0KJ-1H&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1100991292&_rerunOrigin=google&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=95f326bd11a9ec1b91f0ef7876e54efb

**Citations/Other recommended sites**
Authors, Various. "1,8-Bis(dimethylamino)naphthalene". Chemicalbook.com. 11/16/09 .

"Proton Sponge Picture". Wikipedia. 11/18/09 .

Authors, Various. "1,8-Bis(dimethylamino)naphthalene". Wikipedia. 11/18/09 .

Korzhenevska, Nadiya. "Tetrahedron Titles". Science Direct. 11/19/09 .