title: Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas.
abstract: Reduction of nitrobenzene derivatives in the presence of arylureas in aprotic solvents results in large positive shifts in potential of the nitrobenzene(0/)(-) cyclic voltammetry wave with little change in wave shape. This behavior is indicative of reversible hydrogen bonding between nitrobenzene radical anions and arylureas. Computer fitting of the cyclic voltammetry of 4-nitroaniline, NA, plus 1,3-diphenylurea in DMF shows essentially no binding between urea and NA in the oxidized state (K(ox) < 1 M(-)(1)), but very strong binding in the reduced state (K(red) = 8 x 10(4) M(-)(1)), along with very rapid rates of hydrogen bond formation (k(f)'s approximately 10(8)-10(10) M(-)(1) s(-)(1)), making this system a fast on/off redox switch.
authors.affiliation: Department of Chemistry and Biochemistry, San Diego State University, San Diego, California 92182-1030, USA.
authors.forename: Jingjing
authors.initials: J
authors.lastname: Bu
authors.forename: Ninette D
authors.initials: ND
authors.lastname: Lilienthal
authors.forename: Jessica E
authors.initials: JE
authors.lastname: Woods
authors.forename: Cora E
authors.initials: CE
authors.lastname: Nohrden
authors.forename: Kimphuong T
authors.initials: KT
authors.lastname: Hoang
authors.forename: Daniel
authors.initials: D
authors.lastname: Truong
authors.forename: Diane K
authors.initials: DK
authors.lastname: Smith