Crystal structures of two bis(iodomethyl)benzene derivatives: similarities and differences in the crystal packing

McAdam, C. John; Hanton, Lyall R.; Moratti, Stephen C.

doi:10.1107/s2056989015021295

Cited by 2 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of 5a was based on literature methods where the starting materials are also primary alcohols [31,32]. Thus, KI (3.5 g, 21.0 mmol) was added to 4a (3 g, 8.4 mmol) previously dissolved in acetone (40 mL).…”

Section: Synthesis Of Diiodo Compound [{O(c6h4ch2)2}i2] (5a)mentioning

confidence: 99%

See 1 more Smart Citation

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

García-González,

Alvarado-Rodríguez,

Andrade-López

et al. 2024

J. Mex. Chem. Soc.

View full text Add to dashboard Cite

Abstract. In this work, the synthesis and structural study by means of single-crystal X-ray diffraction of compounds of general formula Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I) is reported. These compounds contain two flexible hydrocarbonated arms –CH2–X in the ortho positions to the Ch heteroatom. These compounds were synthesized through a linear synthesis starting from diphenylether or diphenylsulfide. Based on the structural analysis, we describe the more relevant molecular features as well as the non-covalent interactions that the heavy halogen atoms display with other moieties that promote the cohesion of the crystal arrangement. The Hirshfeld analysis displayed that the X···π, X···X, and C–H···X interactions are quite significant in the crystal arrangement. Resumen. En este trabajo, se describen la síntesis y el estudio estructural de difracción de rayos-X de monocristal de seis compuestos con fórmula general Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I), que contienen dos brazos hidrocarbonados flexibles –CH2–X en las posiciones orto al heteroátomo Ch. Estos compuestos fueron sintetizados a través de una síntesis lineal, partiendo de difeniléter o difeniltioéter. A través del análisis estructural se describen las características moleculares más relevantes, así como las interacciones no-covalentes que presentan los átomos de halógeno pesados con otros grupos funcionales para dar cohesión a la red cristalina. El estudio de las superficies de Hirshfeld mostró que las interacciones X···π, X···X y C–H···X son muy relevantes en esta cohesión.

show abstract

Section: Synthesis Of Diiodo Compound [{O(c6h4ch2)2}i2] (5a)mentioning

confidence: 99%

“…Preparation of the title compounds was based on literature methods [31,32]. KI (1.12 g, 6.72 mmol) was added to 4b (1.0 g, 2.69 mmol) dissolved in acetone (25 mL).…”

Section: Synthesis Of Diiodo Compound [{S(c6h4ch2)2}i2] (5b)mentioning

confidence: 99%

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

García-González,

Alvarado-Rodríguez,

Andrade-López

et al. 2024

J. Mex. Chem. Soc.

View full text Add to dashboard Cite

show abstract

1,1′‐Ferrocenylene‐Bridged Bis(N‐Heterocyclic Olefin) Derivatives

et al. 2021

View full text Add to dashboard Cite

The 1,1'-ferrocenylene (fc)-bridged bis(N-heterocyclic olefin) compounds (IMes=CH) 2 fc (1, IMes = 1,3-dimesitylimidazolin-2ylidene) and (IPr=CH) 2 fc (2, IPr = 1,3-bis(2,6diisopropylphenyl)imidazolin-2-ylidene) were synthesised from (ICH 2 ) 2 fc (3) and the respective N-heterocyclic carbene IMes or IPr. Ligand substitution reactions of 1 and 2 with [BH 3 (THF)] afforded the complexes [1(BH 3 ) 2 ] and [2(BH 3 ) 2 ] as mixtures of the rac-and meso-diastereomers. The new ferrocene derivatives 1-3 and the complexes meso-[1(BH 3 ) 2 ], rac-[1(BH 3 ) 2 ] and rac-[2(BH 3 ) 2 ] were structurally characterised by single-crystal X-ray diffraction. 1 and 2 represent a new class of ferrocene-based, and hence redox-active, bidentate ligands. The presence of three redox-active moieties, viz. the ferrocene unit and the two NHO units, is reflected by three consecutive oxidations according to an electrochemical investigation exemplarily performed with 2 by cyclic voltammetry.

show abstract

Crystal structures of two bis(iodomethyl)benzene derivatives: similarities and differences in the crystal packing

Abstract: The molecular and crystal structures of two isomeric bis(iodomethyl)benzene derivatives are reported. A comparison is made of the intermolecular contacts stabilizing the packing in the two closely related systems.

Cited by 2 publications

References 28 publications

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

1,1′‐Ferrocenylene‐Bridged Bis(N‐Heterocyclic Olefin) Derivatives

Contact Info

Product

Resources

About

Crystal structures of two bis(iodomethyl)benzene derivatives: similarities and differences in the crystal packing

Abstract: The mol­ecular and crystal structures of two isomeric bis­(iodo­meth­yl)benzene derivatives are reported. A comparison is made of the inter­molecular contacts stabilizing the packing in the two closely related systems.

Cited by 2 publications

References 28 publications

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface Analysis

1,1′‐Ferrocenylene‐Bridged Bis(N‐Heterocyclic Olefin) Derivatives

Contact Info

Product

Resources

About

Abstract: The molecular and crystal structures of two isomeric bis(iodomethyl)benzene derivatives are reported. A comparison is made of the intermolecular contacts stabilizing the packing in the two closely related systems.