1993
DOI: 10.1139/v93-190
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Crystal chemistry of tetraradial species. Part 3. Salts of aliphatic Schiff bases crystallizable from aqueous media: crystal structures of five iminium tetraphenylborates and a 6-31G* ab initio study of simple iminium ions

Abstract: . Recrystallization of a primary or secondary alkylammonium tetraphenylborate (TB) from approximately 1 : 1 mixtures of Me2C0 (or MeEtCO) and water yields, against expectation, the TB of the corresponding iminium cation and thus provides an easy route to a variety of aliphatic Schiff bases. The crystal structures of five such salts have been de- are discussed in detail, as also is the tendency of the small iminium ions to orientational disorder. The range of the C=N bond length in these and other iminium salts… Show more

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Cited by 17 publications
(13 citation statements)
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“…Easy crystallization of the products can also be attributed to Schiff bases tending to crystallize quite readily from an acetone/water mixture. [14] Such Schiff-base coordination complexes of copper(II) have been drawing attention for some time because of their interesting coordination chemistry and biological applicability. [15,16] We were not able to obtain the chloride complex under similar conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Easy crystallization of the products can also be attributed to Schiff bases tending to crystallize quite readily from an acetone/water mixture. [14] Such Schiff-base coordination complexes of copper(II) have been drawing attention for some time because of their interesting coordination chemistry and biological applicability. [15,16] We were not able to obtain the chloride complex under similar conditions.…”
Section: Resultsmentioning
confidence: 99%
“…[50] The N=C bond length of N,N-dimethylisopropylideneammonium tetraphenylborate (1.30 ) is used as a standard equal to + 1 (a full double bond). [51] The NÀC bond length of 7-(a-(2-methoxycarbonylanilinobenzyl)quinoline-8-ol is taken as a single bond standard (at 1.47 ) and equal to zero charge. [52] Using these standards, a linear correlation is used to assign a charge of + 0.76 for the quaternary nitrogen (Figure 14a).…”
Section: P-electron Density Map Of Ethidiummentioning
confidence: 99%
“…The N=C bond length of both N,N-dimethyl-isopropylideneammonium tetraphenylborate and 9-(10-methyl)acridinium iodide (both 1.30 ) are used as the standards for a double bond and are taken as a + 1 charge. [51,54] Using these standards, charges of + 0.28 and + 0.18 have been assigned to the 3-and 8-amines, respectively (Figure 14a). [55] An early computational study by Giacomoni and Le Bret also predicted positive p-charges for all of ethidiums nitrogen atoms.…”
Section: P-electron Density Map Of Ethidiummentioning
confidence: 99%
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“…Alkyl iminium salts are commercially available, 23 and simple protonated imines have been isolated and are amenable to X-ray crystallographic analysis. 24 Similar ions can be formed from hydrazones, which are typically protonated at the double-bonded nitrogen atom to form stable cations. 25 …”
Section: Introductionmentioning
confidence: 99%