Sterisch überladene Cyclohexane, 3. 4,4,8,8,12,12‐Hexamethyltrispiro[2.1.2.1.2.1]dodecan und 4,4,8,8,9,9,10,10‐Octamethyldispiro[2.1.2.3]decan – Zwei per(cyclo)alkylierte Cyclohexane in Twistbootkonformation

Fitjer, Lutz; Scheuermann, Hans-Jörg; Klages, Ulrich; Wehle, Detlef; Stephenson, David S.; Binsch, Gerhard

doi:10.1002/cber.19861190406

Cited by 28 publications

(4 citation statements)

References 15 publications

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“…• C, 55 which is reflected in the large negative pressure in the constant volume simulation. A fully methylated chain is rare in nature, and therefore, of less relevance in biomolecular simulations.…”

Section: Figure 3 (Top)mentioning

confidence: 99%

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

Schuler¹,

Daura²,

Gunsteren³

2001

J Comput Chem

830

509

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ABSTRACT:Over the past 4 years the GROMOS96 force field has been successfully used in biomolecular simulations, for example in peptide folding studies and detailed protein investigations, but no applications to lipid systems have been published yet. Here we provide a detailed investigation of aliphatic liquid systems. For liquids of larger aliphatic chains, n-heptane and longer, the standard GROMOS96 parameter sets 43A1 and 43A2 yield a too low pressure at the experimental density. Therefore, a reparametrization of the GROMOS96 force field regarding aliphatic carbons was initiated. The new force field parameter set 45A3 shows considerable improvements for n-alkanes, cyclo-, iso-, and neoalkanes and other branched aliphatics. Liquid densities and heat of vaporization are reproduced for almost all of these molecules. Excellent agreement is found with experiment for the free energy of hydration for alkanes. The GROMOS96 45A3 parameter set should, therefore, be suitable for application to lipid aggregates such as membranes and micelles, for mixed systems of aliphatics with or without water, for polymers, and other apolar systems that may interact with different biomolecules.

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Section: Figure 3 (Top)mentioning

confidence: 99%

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

Schuler¹,

Daura²,

Gunsteren³

2001

J Comput Chem

830

509

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“…Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes•, Patai, S., Rappoport, Z., Eds. ; Wiley: Chichester, 1992; Chapter 3. in principle by catalytic hydrogenation of the readily available 1,2,3,4-tetraphenylbenzene (5).10-11…”

mentioning

confidence: 99%

Preparation and Molecular Structure Determination of a 1,2,3,4-Tetracyclohexylcyclohexane Existing in a Twist-Boat Conformation

Columbus¹,

Cohen²,

Biali³

1994

J. Am. Chem. Soc.

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“…The first example of this was the copolymerization of primary and secondary ylides by trialkylboranes (Scheme 2). 15 (Dimethylamino)phenyloxosulfonium ethylide (7) served as a source of the ethylidene group (CHCH 3 ). This monomer was copolymerized with methylide 8 to give a random copolymer poly(ethylidene-co-methylidene) (9), a polymer with the same chemical composition as an ethylene-propylene copolymer.…”

Section: Introductionmentioning

confidence: 99%

“…Functional groups on a hydrocarbon polymer backbone are used to tailor properties such as adhesion, barrier performance, and solvent resistance . The cyclopropyl group can provide a conformational constraint in the polymer backbone and is available for further chemical modification that may facilitate degradation, copolymer formation, or the introduction of other functional groups that modify solubility. − The utility of the cyclopropyl group prompts the design of new methods for the incorporation of this group in synthetic carbon backbone polymers. Direct control of the amount of cyclopropyl groups in the polymer is important to fine-tune polymer properties.…”

Section: Introductionmentioning

confidence: 99%

Repetitive sp³−sp³ Carbon−Carbon Bond-Forming Copolymerizations of Primary and Tertiary Ylides. Synthesis of Substituted Carbon Backbone Polymers: Poly(cyclopropylidine-co-methylidine)

2006

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We report a repetitive sp 3 -sp 3 carbon-carbon bond-forming polymerization for the controlled synthesis of cyclopropyl containing carbon backbone polymers with tailored end groups and molecular weight. Poly(cyclopropylidine-co-methylidine) copolymers (10) were synthesized via copolymerization of (dimethylamino)tolyloxosulfonium cyclopropylide (11) with dimethylsulfonium methylide (8). The polymer was synthesized in M n ranges from 1800 to 6714. The cyclopropyl:methyl incorporation ratios varied from 1:12 and 1:18. The composition of the poly(cyclopropylidine-co-methylidine) polymer ( 10) was established by NMR and IR. GPC revealed a monomodal distribution with PDI between 1.06 and 1.28. The cyclopropyl groups extend the range of functionality that can be incorporated into carbon backbone polymers and illustrate for the first time the use of tertiary ylides as monomers for the polymerization reaction. Direct control of the amount of cyclopropyl groups in the carbon backbone has potential for selective modification of the polymer by, for example, radical ringopening reactions to create new topologies and cross-linking opportunities.

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Sterisch überladene Cyclohexane, 3. 4,4,8,8,12,12‐Hexamethyltrispiro[2.1.2.1.2.1]dodecan und 4,4,8,8,9,9,10,10‐Octamethyldispiro[2.1.2.3]decan – Zwei per(cyclo)alkylierte Cyclohexane in Twistbootkonformation

Cited by 28 publications

References 15 publications

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

Preparation and Molecular Structure Determination of a 1,2,3,4-Tetracyclohexylcyclohexane Existing in a Twist-Boat Conformation

Repetitive sp³−sp³ Carbon−Carbon Bond-Forming Copolymerizations of Primary and Tertiary Ylides. Synthesis of Substituted Carbon Backbone Polymers: Poly(cyclopropylidine-co-methylidine)

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Sterisch überladene Cyclohexane, 3. 4,4,8,8,12,12‐Hexamethyltrispiro[2.1.2.1.2.1]dodecan und 4,4,8,8,9,9,10,10‐Octamethyldispiro[2.1.2.3]decan – Zwei per(cyclo)alkylierte Cyclohexane in Twistbootkonformation

Cited by 28 publications

References 15 publications

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

An improved GROMOS96 force field for aliphatic hydrocarbons in the condensed phase

Preparation and Molecular Structure Determination of a 1,2,3,4-Tetracyclohexylcyclohexane Existing in a Twist-Boat Conformation

Repetitive sp3−sp3 Carbon−Carbon Bond-Forming Copolymerizations of Primary and Tertiary Ylides. Synthesis of Substituted Carbon Backbone Polymers: Poly(cyclopropylidine-co-methylidine)

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Repetitive sp³−sp³ Carbon−Carbon Bond-Forming Copolymerizations of Primary and Tertiary Ylides. Synthesis of Substituted Carbon Backbone Polymers: Poly(cyclopropylidine-co-methylidine)