Synthesis and proton dissociation constants of 2,2'-iminodimethylene dipyridine (2,2'-dipicolylamine)

Romary, J. Kirk; Bunds, Jim E.; Barger, J. D.

doi:10.1021/je60033a018

Cited by 20 publications

(12 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We report here the structure of the perchlorate salt, (I), of the protonated compound. Because the pK a of the amine N atom (determined to be 7.3) is much higher than those of the pyridyl groups (pK a of 2.26 and 1.12) (Romary et al, 1967), the amine N atom is protonated, while the pyridyl N atoms are hydrogen bonded at longer distances. The NÐH bond lengths were constrained to be 0.90 A Ê , with tetrahedral angles about the central amine N atom.…”

Section: Commentmentioning

confidence: 95%

“…The title compound was synthesized by the reaction, at ice temperature, of 2-picolyl chloride and 2-(aminomethyl)pyridine in basic aqueous solution by a literature method (Romary et al, 1967)…”

Section: Methodsmentioning

confidence: 99%

“…

ExperimentalThe title compound was synthesized by the reaction, at ice temperature, of 2-picolyl chloride and 2-(aminomethyl)pyridine in basic aqueous solution by a literature method (Romary et al, 1967)

…”

mentioning

confidence: 99%

See 2 more Smart Citations

Bis(2-pyridylmethyl)ammonium perchlorate

2002

View full text Add to dashboard Cite

Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.006 A Ê Disorder in solvent or counterion R factor = 0.055 wR factor = 0.156 Data-to-parameter ratio = 9.8For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2002 International Union of Crystallography Printed in Great Britain ± all rights reserved ExperimentalThe title compound was synthesized by the reaction, at ice temperature, of 2-picolyl chloride and 2-(aminomethyl)pyridine in basic aqueous solution by a literature method (Romary et al., 1967)

show abstract

Section: Commentmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

See 1 more Smart Citation

Bis(2-pyridylmethyl)ammonium perchlorate

2002

View full text Add to dashboard Cite

show abstract

“…For the study of active sites of enzymes in biological systems as well as in synthetic complexes of interest, see: Davies et al (2004). For the preparation of bis(pyridin-2-ylmethyl)amine (bpa), see: Romary et al (1967). For structures of similar Mn complexes, see: Glerup et al (1992); Gultneh et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

Bis[(2-methylbenzyl)bis(pyridin-2-ylmethyl-κN)amine-κN]manganese(II) bis(perchlorate)

2014

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.006 Å; disorder in main residue; R factor = 0.065; wR factor = 0.193; data-to-parameter ratio = 15.9.In the title complex, [Mn(C 20 H 21 N 3 ) 2 ](ClO 4 ) 2 , two tridentate (2-methylbenzyl)bis(pyridin-2-ylmethyl)amine (L) ligands form the Mn II complex [MnL 2 ](ClO 4 ) 2 . The Mn II ion lies on a twofold axis and the complex cation is significantly distorted from regular octahedral geometry. The packing is stabilized by weak C-HÁ Á ÁO interactions between the cations and anions, which link them into a zigzag ribbon along [101]. The perchlorate anion is disordered and was constrained to be tetrahedral with two orientations having occupancies of 0.768 (4) and 0.232 (4). The 2-methylbenzyl moiety is also disordered over two sets of sites, with occupancies of 0.508 (15) and 0.492 (15). Related literature

show abstract

“…DBA, [7] DPA, [8] TACN, [9] and TACN* [10] are well established in coordination chemistry. PDEA was newly prepared by NaBH 4 reduction of the corresponding Schiff base.…”

Section: Phosphates and Coligandsmentioning

confidence: 99%

Diphosphate−Zinc Complexes with Tridentate Coligands

Groß

Müller-Hartmann

Vahrenkamp

2000

Eur. J. Inorg. Chem.

View full text Add to dashboard Cite

Diorganodiphosphates (POP2−) and a triorgano‐methylenediphosphonate (PCP−) have been combined with zinc salts and the tridentate ligands L [L = bis(benzimidazolylmethyl)amine, bis(2‐pyridylmethyl)amine, triazacyclononane, trimethyltriazacyclononane, and (dimethylaminoethyl)(2‐pyridylmethyl)amine]. The resulting ternary complexes have been found to contain four‐, five‐, or six‐coordinate zinc. Four‐coordinate zinc has been identified in the complex types [L·Zn(PCP)]+ and [L·Zn(POP)Zn·L]2+, containing monodentate phosphate ligands. Five‐coordinate zinc has been found in the complexes [L·Zn(POP)] with chelating diphosphate ligands. Six‐coordinate zinc has been observed in the complex type [L·Zn(POP)·H2O] containing chelating diphosphates and in the complex type [L·Zn(POP)]2 in which the diphosphates act as tridentate bridging ligands. In a few cases, hydrolytic cleavage of the diphosphates resulted in the isolation of the trinuclear complexes [(L·Zn)3(ROPO3)2] HPO4 containing triply‐bridging monophosphates.

show abstract

Synthesis and proton dissociation constants of 2,2'-iminodimethylene dipyridine (2,2'-dipicolylamine)

Abstract: Synthesis of 2,2/-iminodimethylene dipyridine has been accomplished in good yield by reaction of 2-chloromethyl pyridine with excess 2-aminomethyl pyridine. Stepwise

Cited by 20 publications

References 2 publications

Bis(2-pyridylmethyl)ammonium perchlorate

Bis(2-pyridylmethyl)ammonium perchlorate

Bis[(2-methylbenzyl)bis(pyridin-2-ylmethyl-κN)amine-κN]manganese(II) bis(perchlorate)

Diphosphate−Zinc Complexes with Tridentate Coligands

Contact Info

Product

Resources

About