Packing motifs in organic ammonium carboxylate salts: extension of the ring-stacking and ring-laddering concepts

Odendal, James A.; Bruce, Jocelyn C.; Koch, Klaus; Haynes, Delia A.

doi:10.1039/c000922a

Cited by 31 publications

(22 citation statements)

References 17 publications

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“…The ammonium functional group is at an equatorial position to minimize 1,3 and 1,5 di-axial interactions. The bond lengths and bond angles are in the normal ranges and are comparable with those reported earlier for similar compounds (Shimada et al, 1955;Smith et al, 1994;Odendal et al, 2010). Each proton of the ammonium group is hydrogen-bonded to two oxygen atoms of the nitrate ion.…”

Section: Commentsupporting

confidence: 76%

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Lai

Gallucci

2014

Acta Cryst E

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Section: Commentsupporting

confidence: 76%

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Lai

Gallucci

2014

Acta Cryst E

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“…Many of the salts consisting of primary ammonium and carboxylate ions exhibit ladder-type hydrogen-bond networks in the solid state (Sada et al, 2004;Lemmerer et al, 2008a,b,c;Yuge et al, 2008;Bereczki et al, 2009;Odendal et al, 2010;Linares et al, 2010;Lemmerer, 2011;2012a,b;Hisaki et al, 2012;Sasaki et al, 2014). In most of them three H atoms of the primary ammonium ion take part in the formation of laddertype networks with only a R 3 4 ð10Þ hydrogen-bond pattern (Bernstein et al, 1995), which aligns the primary ammonium ions and carboxylates to form 2 1 columns.…”

Section: Effects Of the Ammonium Ion And The Carboxylate On The Formamentioning

confidence: 99%

Structures ofN-acetyl-DL-isoleucine,N-acetyl-DL-alloisoleucine and their ammonium salts; role of ammonium ions in crystal structure formation

Yajima

Kimura

Hori

et al. 2016

Acta Crystallogr Sect B

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The crystal structures of N-acetyl-DL-isoleucine, N-acetyl-DL-alloisoleucine and their ammonium salts show that these four compounds exist as racemic compounds around room temperature. The two ammonium salts are arranged around a 21 screw axis, forming a helical column which consists of ammonium ions and single enantiomeric anions similar to the crystals of the ammonium salts of optically active N-acetyl-L-isoleucine and N-acetyl-D-alloisoleucine. The ammonium ion and the carboxylate ion in the helix are connected by three hydrogen bonds, the fourth hydrogen bond being formed between the ammonium ion and an external acetyl amino group of the neighboring helical column. The fourth hydrogen bond is formed between the ammonium ion and an external acetyl amino group of the neighboring 21 column. Ammonium N-acetyl-DL-alloisoleucinate was revealed to exist as an unstable racemic compound due to conformational similarity between the racemic and optically active compounds in the solid state and was optically resolved by fractional crystallization at 293 K.

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“…Ammonium carboxylate salts of the general formula (RNH 3 + )Á(R 0 COO À ) are known to form hydrogen-bonded one-dimensional ladders in the solid state, among other motifs (Lemmerer et al, 2008a(Lemmerer et al, , 2010. The ladders are composed of hydrogen-bonded rings formed from four N-HÁ Á ÁO hydrogen bonds and consist of two cation-anion pairs (Odendal et al, 2010). The ladders are predominantly of two types, as classified by Nagahama et al (2003): type II consists of repeating hydrogen-bonded rings, described using graph-set notation (Bernstein et al, 1995) as R 3 4 (10), and type III consists of the repetition of two differently sized rings, described as R 2 4 (8) and R 4 4 (12) ( Fig.…”

Section: Commentmentioning

confidence: 99%

Six two- and three-component ammonium carboxylate salt structures with a ladder-type hydrogen-bonding motif, three incorporating neutral carboxylic acid molecules

Lemmerer

2011

Acta Crystallogr C

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Six ammonium carboxylate salts are synthesized and reported, namely 2-propylammonium benzoate, C(3)H(10)N(+)·C(7)H(5)O(2)(-), (I), benzylammonium (R)-2-phenylpropionate, C(6)H(10)N(+)·C(9)H(9)O(2)(-), (II), (RS)-1-phenylethylammonium naphthalene-1-carboxylate, C(8)H(12)N(+)·C(11)H(7)O(2)(-), (III), benzylammonium-benzoate-benzoic acid (1/1/1), C(6)H(10)N(+)·C(7)H(5)O(2)(-)·C(7)H(6)O(2), (IV), cyclopropylammonium-benzoate-benzoic acid (1/1/1), C(3)H(8)N(+)·C(7)H(5)O(2)(-)·C(7)H(6)O(2), (V), and cyclopropylammonium-ea-cis-cyclohexane-1,4-dicarboxylate-ee-trans-cyclohexane-1,4-dicarboxylic acid (2/1/1), 2C(3)H(8)N(+)·C(8)H(10)O(4)(2-)·C(8)H(12)O(4), (VI). Salts (I)-(III) all have a 1:1 ratio of cation to anion and feature three N(+)-H...O(-) hydrogen bonds which form one-dimensional hydrogen-bonded ladders. Salts (I) and (II) have type II ladders, consisting of repeating R(4)(3)(10) rings, while (III) has type III ladders, in this case consisting of alternating R(4)(2)(8) and R(4)(4)(12) rings. Salts (IV) and (V) have a 1:1:1 ratio of cation to anion to benzoic acid. They have type III ladders formed by three N(+)-H...O(-) hydrogen bonds, while the benzoic acid molecules are pendant to the ladders and hydrogen bond to them via O-H...O(-) hydrogen bonds. Salt (VI) has a 2:1:1 ratio of cation to anion to acid and does not feature any hydrogen-bonded ladders; instead, the ionized and un-ionized components form a three-dimensional network of hydrogen-bonded rings. The two-component 1:1 salts are formed from a 1:1 ratio of amine to acid. To create the three-component salts (IV)-(VI), the ratio of amine to acid was reduced so as to deprotonate only half of the acid molecules, and then to observe how the un-ionized acid molecules are incorporated into the ladder motif. For (IV) and (V), the ratio of amine to acid was reduced to 1:2, while for (VI) the ratio of amine to acid required to deprotonate only half the diacid molecules was 1:1.

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Packing motifs in organic ammonium carboxylate salts: extension of the ring-stacking and ring-laddering concepts

Cited by 31 publications

References 17 publications

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

N-[2-(9H-Carbazol-9-yl)ethyl]-4-(methylsulfonyl)aniline

Structures ofN-acetyl-DL-isoleucine,N-acetyl-DL-alloisoleucine and their ammonium salts; role of ammonium ions in crystal structure formation

Six two- and three-component ammonium carboxylate salt structures with a ladder-type hydrogen-bonding motif, three incorporating neutral carboxylic acid molecules

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