Lipophilicity Enhancing Substituents for ADDA Recognition Domains of DAAD·ADDA Heterodimers with Quadruple Hydrogen Bonds | Zendy

Otte Philipp | Zendy; Taubitz Jörg | Zendy; Lüning Ulrich | Zendy

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Lipophilicity Enhancing Substituents for ADDA Recognition Domains of DAAD·ADDA Heterodimers with Quadruple Hydrogen Bonds

Author(s) -

Otte Philipp,

Taubitz Jörg,

Lüning Ulrich

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201201450

Subject(s) - chemistry , hydrogen bond , alkyl , amide , pyrimidinones , intramolecular force , lipophilicity , stereochemistry , molecular recognition , molecule , polyethylene glycol , crystallography , organic chemistry

Four new ADDA receptors for DAAD · ADDA heterodimer formation by quadruple hydrogen bonds have been prepared. Their solubility has been improved by substitution with polyethylene glycol or branched alkyl chains. Three ADDA urea structures 8 , 9 , and 10 possess stabilizing intramolecular hydrogen bonds, in contrast to a related amide 7 . The association constants K ass span several orders of magnitudes, with pyrimidinones 8 and 9 showing K ass values above 10 4 M –1 .

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