Lactones. 1. X-ray crystallographic studies of nonanolactone and tridecanolactone: nature of CH.cntdot..cntdot..cntdot.O nonbonded interactions

Wiberg, Kenneth B.; Waldron, Roy F.; Schulte, Gayle K.; Saunders, Martin

doi:10.1021/ja00003a034

Cited by 76 publications

(45 citation statements)

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“…The C-H-..O angle of 108.0(8)" in 11 is similar to the corresponding value of 109.5" in nonanolactone (25). Including these C-H...O hydrogen bonds, the complete three-dimensional array of the crystalline form of 11 has an approximate diamond-lattice conformation resembling the skeleton of "diamantane" ("congressane") (26).…”

Section: Resultssupporting

confidence: 52%

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Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane

Kliegel¹,

Lubkowitz²,

Rettig³

et al. 1992

Can. J. Chem.

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. Can. J. Chem. 70, 2809 (1 992). The preparation of the N-(2-hydroxypropy1)-N-alkylhydroxylamines, 6 a (R = CH,) and 6b (R = CH,Ph), and their reactions with phenylboronic acid are described. Regardless of the molar ratios of reactants employed, the reaction with 6b leads to the 1 : 2 condensate 1-benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-l -azonia-3-bora-5-boratabicyclo[3.3.0]-octane, 7, while that with 6 a gives rise to the 1 : 1 condensate 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-l,6-diazonia-2,7-diboratatricyclo[5.3.1. 1'.6jdodecane, 11 (the cyclic BONBON dimer of 4,6-dimethyl-2-phenyl-1,3-dioxa-4-aza-2-boracyclohexane, 9). Compounds 7 and 11 both crystallize in the triclinic space group p i : for 7; a = 13.126(1), b = 15.337(1), c = 10.9469(5)0A, a = 91.727(5), P = 104.647(5), y = 72.922(7)", Z = 4; and for 11; a = 9.0807(4), b = 9.1653(3), c = 6.4876(2) A, a = 97.708(3), P = 108.830(3), y = 89.188(4)", Z = 1. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.038 and 0.032 for 5879 and 1827 reflections with I 2 3u( F '), respectively. Compound 7 has the expected bicyclic pyroboronate structure, but represents the first reported N-substituted example of this type of compound. Bond lengths involving boron in 7 are (C) @-~(sp~) = 1.428(2) and 1.420 (2) [Traduit par la redaction]

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Section: Resultssupporting

confidence: 52%

“…The dimeric structure of 11 in the solid state is additionally stabilized by weak transannular C-H-a.0 hydrogen bonds between C(2)-H (3) (25). The C-H-..O angle of 108.0(8)" in 11 is similar to the corresponding value of 109.5" in nonanolactone (25).…”

Section: Resultsmentioning

confidence: 82%

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane

Kliegel¹,

Lubkowitz²,

Rettig³

et al. 1992

Can. J. Chem.

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“…O hydrogen bonds are frequently reported since the statistical study of the Cambridge Data Base by Taylor and Kennard [17]. These interactions involve activated aromatic C--H groups, alkyne or alkene C--H groups, activated aliphatic C--H groups [18], and even unactivated aliphatic C--H groups [19]. A possible role of C--H" 9 9 O interactions in drug-receptor binding of Zopiclone, a powerful benzodiazepin receptor agonist, has been postulated [20].…”

Section: Resultsmentioning

confidence: 99%

“…Semiempirical M* calculations like AM 1 or PM3 give access to atomic charges at low cost, and we there- (19) 138(3)* 132.3" 151.8* fore planned to use these charges to estimate the propensity of hydrogen atoms to form C--H 9 9 9 O hydrogen bonds. A similar approach, using STO-5G charges to explain cocrystal formation with diaryl ureas, was recently published [23].…”

Section: Resultsmentioning

confidence: 99%

Crystal and molecular structure analysis of flutamide. Bifurcated helicoidal C-H ⋯ O hydrogen bonds

Cense

Agafonov²,

Céolin³

et al. 1994

Struct Chem

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Crystal structure determination and semiempirical AM 1 and PM3 calculations were performed on flutamide {2-methyl-N[4 nitro-3-(trifluoromethyl) phenyl] propamide}, a powerful nonsteroidal androgen antagonist. The molecule is almost planar apart from CF3, NO2, and CH 3 groups. The NO 2 plane makes an angle of 36.3(4) ~ with the least-square plane of the phenyl ring. The molecules are intermoleculady linked by one N--H-9 9 O and one C--H 9 9 9 O hydrogen bonds. A bifurcated helicoidal hydrogen bond network is formed by the intermolecular C--H 9 9 9 O hydrogen bond together with another intramolecular C--H 9 9 9 O hydrogen bond. The calculated structures are in good agreement with the crystallographic conformations. AM 1 is more accurate for predicting the intramolecular C--H 9 9 9 O hydrogen bond while PM3 gives a better geometry for the crowded nitro group. AMI and PM3 charges of benzenic hydrogens are used to predict the propensity of these atoms to form hydrogen bonds. The noncentrosymmetric space group of the crystal (Pna20, the calculated dipole moment (8.88 D), and the calculated angle between molecular dipoles and the twofold axis (-49 ~ close to the optimal value (54.7 ~ indicate that flutamide might be a possible candidate for nonlinear optical material.

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“…[10] X-ray crystallographic studies of cyclotetradecane, [11] cyclotetradecanone, [12] cyclotetradecane oxime, [13] 1,3,8,10-tetraoxacyclotetradecane, [14] and 13-tridecanolide [15] prove the preference for the [3434] conformation as lowest-energy conformer. A recent conformation analysis of methyl-substituted 14-membered macrocycles by DNMR (Dynamic Nuclear Magnetic Resonance) spectroscopy also confirmed the preference for [3434] conformations in solution.…”

Section: Introductionmentioning

confidence: 99%

Constructing Conformationally Constrained Macrobicyclic Musks

Kraft

Cadalbert

2001

Chemistry A European J

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To investigate the structure-odor correlation of musks, (12R)-12-methyl-13-tridecanolide (1), a macrocyclic musk, and 13-tridecanolide, its non-musky demethyl analogue, were conformationally constrained by introduction of methylene bridges between C-3 and C-8 or C-9. These [7.5.1]- and [8.4.1]-macrobicycles were synthesized starting from bicyclo[5.3.1]undec-8-en-9-one (3) and bicyclo[4.3.1]dec-7-en-8-one (8), respectively, by a sequence consisting of catalytic hydrogenation, alpha-alkylation with a TBS-protected (tert-butyldimethylsilyl) hydroxy halide, acid-catalyzed cyclization, oxidative cleavage of the formed enol ether double bond, and subsequent reduction of the carbonyl group via its tosylhydrazone. The compound (1R,6R,9R)-(+)-6-methyl-4-oxa-bicyclo[7.5.1]pentadecan-3-one (22) was found to possess the most pronounced musk odor, and this was rationalized by a superposition analysis with the polycyclic aromatic musk odorant (4S,7R)-Galaxolide (2). In its (1S,6R,9S)-(+)-stereoisomer 23 as well as in (1S,6R, 10R)-(+)-6-methyl-4-oxabicyclo[8.4.1]-pentadecan-3-one (18) the (6R)-methyl group seems to hinder the interaction with the musk receptor, while the demethyl compounds 7 and 12 showed only very faint odors.

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Lactones. 1. X-ray crystallographic studies of nonanolactone and tridecanolactone: nature of CH.cntdot..cntdot..cntdot.O nonbonded interactions

Cited by 76 publications

References 1 publication

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane

Crystal and molecular structure analysis of flutamide. Bifurcated helicoidal C-H ⋯ O hydrogen bonds

Constructing Conformationally Constrained Macrobicyclic Musks

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Lactones. 1. X-ray crystallographic studies of nonanolactone and tridecanolactone: nature of CH.cntdot..cntdot..cntdot.O nonbonded interactions

Cited by 76 publications

References 1 publication

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.12,6]dodecane

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.12,6]dodecane

Crystal and molecular structure analysis of flutamide. Bifurcated helicoidal C-H ⋯ O hydrogen bonds

Constructing Conformationally Constrained Macrobicyclic Musks

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Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane

Structural studies of organoboron compounds. LVI. 1-Benzyl-7-methyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane and 1,4,6,9-tetramethyl-2,7-diphenyl-3,8,11,12-tetraoxa-1,6-diazonia-2,7-diboratatricyclo[5.3.1.1^2,6]dodecane