Effect of cosolvent on the lateral order of spontaneously formed amphiphilic amide two-dimensional crystallites at the air-solution interface

Weinbach, Susan P.; Jacquemain, D.; Leveiller, F.; Kjær, Kristian; Als‐Nielsen, J.; Leiserowitz, Leslie

doi:10.1021/ja00077a007

Cited by 35 publications

(24 citation statements)

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“…The corresponding dihedral angles amount to 144.3° (C25−C24−C26−O27) and −27.2° (C5−C4−C6−O7), respectively. This deviation from coplanarity of the carboxamide and cyclopentadienyl π-systems is probably due to hydrogen bonding between the carboxamide functions in complex 6d . In the crystal, 6d forms two types of hydrogen bonds: an intramolecular one between H28 and O7 (calculated separation = 2.181 Å) and an intermolecular hydrogen bond (2.131 Å = calculated distance between H8 and O27*).…”

Section: Resultsmentioning

confidence: 96%

The Isocyanate Route to Cyclopentadienyl-Carboxamide- and Cyclopentadienyl-Amino Ester-Substituted Metallocene Complexes

et al. 1996

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Lithium cyclopentadienide adds to a variety of isocyanates [R−NCO, R = tert-butyl (a), n-butyl (b), cyclohexyl (c), phenyl (d), 3-pyridyl (e), 2-tetrahydropyranyl (f), adamantyl (g)] to yield the monocarbamoyl-substituted cyclopentadienides C5H4CONHR- 3 admixed with varying amounts of the respective 1,2-dicarbamoyl-substituted C5H3(CONHR)2 - systems 4 and a corresponding quantity of the C5H5 - starting material. Subsequent treatment of these reaction mixtures with anhydrous FeCl2 gave the 1,1‘-dicarbamoylferrocenes 6 and the corresponding monocarbamoylferrocenes 5, which were easily separated by chromatography. The carbamoylferrocenes 5b, 5c, and 6d were characterized by X-ray crystal structure analyses. The (N-phenyl- and (N-adamantylcarbamoyl)cyclopentadienides were treated with CpTiCl3 to give the carboxamide-substituted titanocene dichloride complexes [Cp(C5H4CONHR)TiCl2] 8a (R = Ph) and 8b (R = adamantyl), respectively. Complex 8b was also characterized by X-ray diffraction. The valine ester-derived isocyanate reacts with lithium cyclopentadienide to give the N-valinyl-substituted carbamoylcyclopentadienide 3h. Subsequent treatment with FeCl2 or FeCl2/CpLi, respectively, produces the 1,1‘-difunctionalized ferrocene 6h or the monofunctionalized ferrocene 5h. Both complexes were characterized by X-ray crystal structure analyses.

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Section: Resultsmentioning

confidence: 96%

The Isocyanate Route to Cyclopentadienyl-Carboxamide- and Cyclopentadienyl-Amino Ester-Substituted Metallocene Complexes

et al. 1996

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“…The second example involves the different hydrogenbonding properties of the cosolvents formamide (HCONH2) and formic acid (HCO2H) in aqueous solution, which have a drastic effect on the crystallinity and structure of films of aliphatic amides and carboxylic acids (Weinbach et al, 1993). Arachidamide, C19H39CONH2, on pure water forms a crystalline monolayer according to the Bragg peaks displayed by the GID pattern ( Fig.…”

Section: Effect Of Solvent and Tailor-made Auxiliaries On Growth Dismentioning

confidence: 99%

Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using `tailor-made' auxiliaries

Weissbuch¹,

Popovitz‐Biro²,

Lahav³

et al. 1995

Acta Crystallogr B Struct Sci

332

288

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Tailor-made auxiliaries for the control of nucleation and growth of molecular crystals may be classified into two broad categories: inhibitors and promoters. Tailor-made inhibitors of crystal growth can be used for a variety of purposes, which include morphological engineering and etching, reduction of crystal symmetry, assignment of absolute structure of chiral molecules and polar crystals, elucidation of the effect of solvent on crystal growth, and crystallization of a desired polymorph. As for crystal growth promoters, monolayers of amphiphilic molecules on water have been used to induce the growth of a variety of three-dimensional crystals at the monolayer-solution interface by means of structural match, molecular complementarity or electrostatic interaction. A particular focus is made on the induced nucleation of ice by mono- © 1995 International Union of Crystallography Printed in Great Britain -all fights reserved layers of water-insoluble aliphatic alcohols. The twodimensional crystalline structures of such monolayers have been studied by grazing incidence X-ray diffraction. It has become possible to monitor, by this method, the growth, dissolution and structure of self-aggregated crystalline monolayers, and indeed multilayers, affected by the interaction of solvent molecules in the aqueous subphase with the amphiphilic headgroups, and by the use of tailor-made amphiphilic additives.

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“…It was shown that the clusterization process is very sensitive to temperature, pH, and different additives in the subphase. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Despite numerous experimental studies on different factors, particularly the temperature in the process of monolayer formation, there are less theoretical models capable of predicting the aggregation behavior of amphiphiles (cf. for example, ref.…”

mentioning

confidence: 99%

“…Using the calculated array of data for Gibbs' energies of the amphiphile clusterization at 278 K, 298 K, 318 K it is possible to construct the correlation dependence of DG Cl T,N /m on the temperature and K a,N /m using scheme 2. Considering the statistical insignificance of several coefficients in eqn (5) this dependence can be expressed as follows:…”

mentioning

confidence: 99%

A quantum chemical model for assessment of the temperature dependence in monolayer formation of amphiphiles at the air/water interface

Vysotsky

Fomina

Fainerman

et al. 2013

Phys. Chem. Chem. Phys.

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In the present study it is shown that parameters used in the framework of the model for the assessment of the threshold temperature of spontaneous clusterization of nonionic amphiphiles at the air/water interface (T(Cl)) are independent of the amphiphile type used in the developed schemes. The temperature dependence of the clusterization Gibbs' energies of alkyl amides, α-amino acids and 2-hydroxycarboxylic acids obtained in the framework of several schemes is listed. The exploited schemes differ from each other by the degree of their theoretical validity. The values of the clusterization threshold temperature for substituted alkanes can be described by a fractionally linear function versus the number of CH···HC interactions in the framework of the simplest scheme taking into account the found corrections and agree well with available experimental data.

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Effect of cosolvent on the lateral order of spontaneously formed amphiphilic amide two-dimensional crystallites at the air-solution interface

Cited by 35 publications

References 0 publications

The Isocyanate Route to Cyclopentadienyl-Carboxamide- and Cyclopentadienyl-Amino Ester-Substituted Metallocene Complexes

The Isocyanate Route to Cyclopentadienyl-Carboxamide- and Cyclopentadienyl-Amino Ester-Substituted Metallocene Complexes

Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using `tailor-made' auxiliaries

A quantum chemical model for assessment of the temperature dependence in monolayer formation of amphiphiles at the air/water interface

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