A. Filarowski

Symmetry/Asymmetry of the NHN Hydrogen Bond in Protonated 1,8-Bis(dimethylamino)naphthalene

Experimental and theoretical results are presented based on vibrational spectra and motional dynamics of 1,8-bis(dimethylamino)naphthalene (DMAN) and its protonated forms (DMANH+ …

p.-piekos
How strong is hydrogen bonding to the amide nitrogen? featured image

How strong is hydrogen bonding to the amide nitrogen?

The protonation of the carboxamide nitrogen atom is an essential part of in vivo and in vitro processes (cis-trans isomerization, amides hydrolysis etc). This phenomenon is well …

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Dr. Vladimir Mikshiev

1,8-Bis(dimethylamino)naphthyl-2-ketimines: Inside vs outside protonation

The structure and protonation behaviour of four ortho-arylketimines of 1,8-bis(dimethylamonio)naphthalene with a different number of methoxy groups in an aromatic substituent were …

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Dr. Alexander Antonov
Reaction of 2-Trifluoroacetyl-1,8-Bis(dimethylamino)naphthalene with Strong Organic Bases: Acidic Ionization of 1-NMe2 Group Resulting in the Formation of Benzo[g]indole Derivatives versus Nucleophilic Addition to C=O Group featured image

Reaction of 2-Trifluoroacetyl-1,8-Bis(dimethylamino)naphthalene with Strong Organic Bases: Acidic Ionization of 1-NMe2 Group Resulting in the Formation of Benzo[g]indole Derivatives versus Nucleophilic Addition to C=O Group

A novel approach to pyrrole ring closure in 2-trifluoroacetyl- and 2-ethoxycarbonyl-1,8-bis(dimethylamino)naphthalenes via treatment with …

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Dr. Alexander Antonov
Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the „proton sponge coin” featured image

Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the „proton sponge coin”

It has been found that 1,8-bis(dimethylamino)naphthalene (DMAN), unlike N,N-dimethylaniline, undergoes ring metallation in the n-BuLi–TMEDA–Et2O system with a low selectivity and …

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Dr. Alexander Antonov
Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives featured image

Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives

1,8-Bis(dimethylamino)naphthalenes bearing 2-positioned trifluoroacetyl or ethoxycarbonyl group on treatment with 2-lithio-1,8-bis-dimethylamino)naphthalene undergo base-promoted …

kachalkina
Out-Basicity of 1,8-bis(dimethylamino)naphthalene: The experimental and theoretical challenge featured image

Out-Basicity of 1,8-bis(dimethylamino)naphthalene: The experimental and theoretical challenge

A possibility of non-conventional two-step protonation of 1,8-bis(dimethylamino)naphthalene (proton sponge) is discussed. Unlike the generally accepted mechanism, involving …

v.-a.-ozeryanskii