The Formic Acid 1D Array with H Bonds All Reversed:  Structure of a Cocrystal with Hydrogen Fluoride<sup>1,2</sup>

Wiechert, Dirk; Mootz, and Dietrich; Dahlems, Thomas

doi:10.1021/ja972337f

Cited by 31 publications

(17 citation statements)

References 8 publications

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“…A number of catemers, or open chains of various types ( C1 – C5 ), exist. In C1 , C2 and C3 , all the molecules are syn ; C4 is obtained by switching the H atoms in C2 and is anti throughout,19, 20 whereas C5 contains alternating syn and anti molecules. All these catemers are 1D patterns.…”

Section: Resultsmentioning

confidence: 99%

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Das

Desiraju

2006

Chemistry An Asian Journal

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The catemer is an infinite one-dimensional pattern formed by the carboxylic acid group in crystals, and is constituted with O-H...O hydrogen bonds. The catemer is uncommon and may be contrasted with the ubiquitous carboxylic acid dimer, the favored mode of association of this functional group. Both catemers and dimers, however, have two O-H...O hydrogen bonds for each carboxy group, so the reasons for the rarity of the catemer must lie elsewhere. In this paper, we describe a group of around 25 phenylpropiolic acids in which the catemer is the default packing mode. Exceptionally, the particular catemer that is found in this family is of the very rare syn,anti variety. We show that a necessary ingredient in catemer formation is a supportive C-H...O hydrogen bond from a proximal C-H group, which is located on the phenyl ring, ortho to the ethynyl group, and suitably activated by electron withdrawing substituents. When steric factors become noteworthy, alternative patterns are adopted, such as the syn,syn catemer and, in one case, a rare cisoid dimer. When electron-donating groups, either through inductive effect such as methyl or through resonance such as halogens, are present on the phenyl ring, the dimer is formed in all but one case. Polymorphism seems not to be an issue in these carboxylic acids in that no compound would generally crystallize as both a dimer and a catemer. It may be concluded that a supporting interaction, in this case a C-H...O hydrogen bond, is the essential condition for the formation of any carboxylic acid catemer. Catemers are so rare because it is difficult to set up this type of supporting interaction in most carboxylic acids.

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Section: Resultsmentioning

confidence: 99%

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Das

Desiraju

2006

Chemistry An Asian Journal

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“…Ordered syn±anti chains are also present in other cubane carboxylic acids (Ermer & Lex, 1987) and seem to be the dominant pattern in that class of compounds, despite occurring for an estimated 0.15% of all organic carboxylic acids (Kuduva et al, 1999). The existence of the antiplanar conformation in the carboxyl group of the cubane acids was attributed to its allowance of CÐHÁ Á ÁO hydrogen bonding involving the acidic cubane H atoms, an idea which is supported by the structure of formic acid±HF (Wiechert et al, 1997), which is able to form CÐHÁ Á ÁO hydrogen bonds in conjunction with anti±anti carboxyl chains. The role of CÐ HÁ Á ÁO hydrogen bonding in allowing the less stable anti carboxyl group conformation in (I) is less clear.…”

Section: Figurementioning

confidence: 90%

Disorderedsyn–antihydrogen-bonded chains in 3-(ferrocenylcarbonyl)propionic acid

2003

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“…[28] are also included in the fourth group. There are also many examples of nonmetallic compounds as (C 6 H 5 ) 3 PO·HF [29], C 5 H 5 N·nHF(pyridine-HF complexes with n = 2, 3, 4, 6) [30,31], HCOOH·HF [32], Et 3 N·nHF (n = 3, 4) Me 3 N·nHF (n = 3,4,5,7) [31], etc., with O/N···H-F hydrogen bonds, which also cannot be classified in one of the previous groups because they neither contain [H n F n+1 ] -species (Group I) nor exclusively F···H-F hydrogen bonds (Groups II and III).…”

Section: Crystal Structure Of Cosr 5 (Asf 6 ) 12 ·8hfmentioning

confidence: 99%

Crystal structures of KM(AsF₆)₃ (M²⁺ = Mg, Co, Mn, Zn), KCu(SbF₆)₃ and [Co(HF)₂]Sr[Sr(HF)]₂[Sr(HF)₂]₂[AsF₆]₁₂

Mazej

Goreshnik

2014

Zeitschrift Für Kristallographie - Crystalline Materials

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The KM(AsF 6 ) 3 (M 2+ = Mg, Co, Mn, Zn) and KCu(SbF 6 ) 3 compounds crystallize isotypically to previously known KNi(AsF 6 ) 3 . The main features of the structure of these compounds are rings of MF 6 octahedra sharing apexes with AsF 6 octahedra connected into infinite tridimensional frameworks. In this arrangement cavities are formed where K + cations are placed. Single crystals of CoSr 5 (AsF 6 ) 12 ·8HF were obtained as one of the products after the crystallization of 3KF/CoF 2 /SrF 2 mixture in the presence of AsF 5 in anhydrous HF. The CoSr 5 (AsF 6 ) 12 ·8HF is monoclinic, C/2c (No.15), with a = 26.773(5) Å, b = 10.087(2) Å, c = 21.141(5) Å, β = 93.296(13) °, V = 5699.9(19) Å 3 at 200 K, and Z = 4. There are three crystallographically non-equivalent Sr 2+ cations in the crystal structure of CoSr 5 (AsF 6 ) 12 ·8HF. The Sr1 is coordinated by ten fluorine atoms from eight different [AsF 6 ] -anions, meanwhile Sr2 and Sr3 are bound to nine fluorine atoms provided by one HF and eight AsF 6 units or by two HF and six AsF 6 units, respectively. The Co 2+ is coordinated distorted-octahedrally by six fluorine atoms from two HF molecules and four different AsF 6 units. All those moieties in the crystal strucutre of [Co(HF) 2 ]Sr[Sr(HF)] 2 [Sr(HF) 2 ] 2 -[AsF 6 ] 12 are connected into tridimensional framework. The CoSr 5 (AsF 6 ) 12 ·8HF is a unique example of compound where HF molecules are directly bound via fluorine atoms to two different metal centres.

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The Formic Acid 1D Array with H Bonds All Reversed: Structure of a Cocrystal with Hydrogen Fluoride^1,2

Cited by 31 publications

References 8 publications

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Disorderedsyn–antihydrogen-bonded chains in 3-(ferrocenylcarbonyl)propionic acid

Crystal structures of KM(AsF₆)₃ (M²⁺ = Mg, Co, Mn, Zn), KCu(SbF₆)₃ and [Co(HF)₂]Sr[Sr(HF)]₂[Sr(HF)₂]₂[AsF₆]₁₂

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The Formic Acid 1D Array with H Bonds All Reversed: Structure of a Cocrystal with Hydrogen Fluoride1,2

Cited by 31 publications

References 8 publications

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Packing Modes in Some Mono‐ and Disubstituted Phenylpropiolic Acids: Repeated Occurrence of the Rare syn,anti Catemer

Disorderedsyn–antihydrogen-bonded chains in 3-(ferrocenylcarbonyl)propionic acid

Crystal structures of KM(AsF6)3 (M2+ = Mg, Co, Mn, Zn), KCu(SbF6)3 and [Co(HF)2]Sr[Sr(HF)]2[Sr(HF)2]2[AsF6]12

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The Formic Acid 1D Array with H Bonds All Reversed: Structure of a Cocrystal with Hydrogen Fluoride^1,2

Crystal structures of KM(AsF₆)₃ (M²⁺ = Mg, Co, Mn, Zn), KCu(SbF₆)₃ and [Co(HF)₂]Sr[Sr(HF)]₂[Sr(HF)₂]₂[AsF₆]₁₂