Cheminformatics Classic #1

H. Wiener, Structural Determination of Paraffin Boiling Points, Journal of the American Chemical Society, 1947, 69:1, 17-20, doi:10.1021/ja01193a005.

Table I: Normal Paraffins

Cpd. t0 w0 p0 SMILES
n-Butane -0.5 10 1 CCCC
n-Pentane 36.1 20 2 CCCCC
n-Hexane 68.7 35 3 CCCCCC
n-Heptane 98.4 56 4 CCCCCCC
n-Octane 125.7 84 5 CCCCCCCC
n-Nonane 150.8 120 6 CCCCCCCCC
n-Decane 174.0 165 7 CCCCCCCCCC
n-Undecane 195.8 220 8 CCCCCCCCCCC
n-Dodecane 216.2 286 9 CCCCCCCCCCCC

Where t0 is the boiling point.

Table II (Derived)

Cpd. t0 SMILES
n-Butane -0.5 CCCC
2-Methylpropane 10.7 CC(C)C
n-Pentane 36.1 CCCCC
2-Methylbutane 44.3 CC(C)CC
2,2-Dimethylpropane 62.7 CC(C)(C)C
n-Hexane 68.7 CCCCCC
2-Methylpentane 77.2 CC(C)CCC
3-Methylpentane 74.1 CCC(C)CC
2,2-Dimethylbutane 87.7 CC(C)(C)CC
2,3-Dimethylbutane 79.5 CC(C)C(C)C
n-Heptane 98.4 CCCCCCC
2-Methylhexane 106.8 CC(C)CCCC
3-Methylhexane 104.9 CCC(C)CCC
3-Ethylpentane 103.4 CCC(CC)CC
2,2-Dimethylpentane 117.6 CC(C)(C)CCC
2,3-Dimethylpentane 107.1 CC(C)C(C)CC
2,4-Dimethylpentane 116.3 CC(C)CC(C)C
3,3-Dimethylpentane 110.8 CCC(C)(C)CC
2,2,3-Trimethylbutane 115.9 CC(C)(C)C(C)C

Table III: Nonanes and Decanes

Cpd. tobs. SMILES
n-Nonane 150.8 CCCCCCCCC
2-Methyloctane 143.3 CC(C)CCCCCC
3-Methyloctane 144.2 CC(CC)CCCCC
4-Methyloctane 142.5 CC(CCC)CCCC
3-Ethylheptane 143.0 C(C)C(CC)CCCC
4-Ethylheptane 141.2 C(C)C(CCC)CCC
2,2-Dimethylheptane 130.5 CC(C)(CCCCC)C
2,3-Dimethylheptane 140.5 CC(C)C(CCCC)C
2,4-Dimethylheptane 133 CC(C)CC(CCC)C
2,5-Dimethylheptane 136 CC(C)CCC(CC)C
2,6-Dimethylheptane 135.2 CC(C)CCCC(C)C
3,3-Dimethylheptane 137.3 CC(CC)(CCCC)C
3,4-Dimethylheptane 140.5 CC(CC)C(CCC)C
2-Methyl-3-ethylhexane 139 CC(C)C(CCC)CC
2,2,3-Trimethylhexane 133.4 CC(C)(C(CCC)C)C
2,2,4-Trimethylhexane 126.5 CC(C)(CC(CC)C)C
2,2,5-Trimethylhexane 124.1 CC(C)(CCC(C)C)C
2,3,3-Trimethylhexane 138 CC(C)C(CCC)(C)C
2,3,5-Trimethylhexane 131.4 CC(C)C(CC(C)C)C
2,4,4-Trimethylhexane 131 CC(C)CC(CC)(C)C
3,3,4-Trimethylhexane 139 CC(CC)(C(CC)C)C
3,3-Diethylpentane 146.5 C(C)C(CC)(CC)CC
2,2-Dimethyl-3-ethylpentane 133.8 CC(C)(C(CC)CC)C
2,3-Dimethyl-3-ethylpentane 142 CC(C)C(CC)(CC)C
2,4-Dimethyl-3-ethylpentane 136.7 CC(C)C(C(C)C)CC
2,2,3,3-Tetramethylpentane 140.2 CC(C)(C(CC)(C)C)C
2,2,3,4-Tetramethylpentane 133.0 CC(C)(C(C(C)C)C)C
2,2,4,4-Tetramethylpentane 122.3 CC(C)(CC(C)(C)C)C
2,3,3,4-Tetramethylpentane 141.5 CC(C)C(C(C)C)(C)C
n-Decane 174.0 CCCCCCCCCC
2-Methylnonane 166.8 CC(C)CCCCCCC
3-Methylnonane 167.8 CC(CC)CCCCCC
4-Methylnonane 165.7 CC(CCC)CCCCC
5-Methylnonane 165.1 CC(CCCC)CCCC
2,4-Dimethyloctane 153.2 CC(C)CC(CCCC)C
2,5-Dimethyloctane 159 CC(C)CCC(CCC)C
2,6-Dimethyloctane 160 CC(C)CCCC(CC)C
2,7-Dimethyloctane 160.2 CC(C)CCCCC(C)C
3,3-Dimethyloctane 161.2 CC(CC)(CCCCC)C
3,6-Dimethyloctane 160.8 CC(CC)CCC(CC)C
4,5-Dimethyloctane 161.0 CC(CCC)C(CCC)C
4-n-Propylheptane 161.7 C(CC)C(CCC)CCC
4-Isopropylheptane 158.6 C(C)(C)C(CCC)CCC
2-Methyl-5-ethylheptane 158.4 CC(C)CCC(CC)CC
3-Methyl-3-ethylheptane 156.3 CC(CC)(CCCC)CC
2,2,4-Trimethylheptane 147 CC(C)(CC(CCC)C)C
2,2,6-Trimethylheptane 148.9 CC(C)(CCCC(C)C)C
2,3,3-Trimethylheptane 160 CC(C)C(CCCC)(C)C
2,3,6-Trimethylheptane 155.3 CC(C)C(CCC(C)C)C
2,4,4-Trimethylheptane 151 CC(C)CC(CCC)(C)C
2,4,6-Trimethylheptane 147.6 CC(C)CC(CC(C)C)C
2,5,5-Trimethylheptane 152.8 CC(C)CCC(CC)(C)C
3,4-Diethylhexane 160.7 C(C)C(CC)C(CC)CC
2,2-Dimethyl-4-ethylhexane 148 CC(C)(CC(CC)CC)C
2,2,3,4-Tetramethylhexane 156.5 CC(C)(C(C(CC)C)C)C
2,2,4,5-Tetramethylhexane 145.8 CC(C)(CC(C(C)C)C)C
2,2,5,5-Tetramethylhexan 136.8 CC(C)(CCC(C)(C)C)C
All data on this page is available under CC0, but the document itself is available under CC-SA-BY. Contributors: Egon Willighagen.
Users of this data are kindly asked to cite this project: E.L. Willighagen, Cheminformatics Classics, 2010. Available from http://github.com/egonw/cheminformatics.classics/.

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