Hydrocarbons: An Introduction to Structure, Physico-Chemical Properties and Natural Occurrence
Hydrocarbons are among the most abundant organic compound classes in the biogeosphere. They are formed directly by living organisms as biosynthetic products or through geological transformation of biomass in sedimentary systems. This article provides an introduction to the structural variability of hydrocarbons and their occurrence in natural environments. Besides saturated, unsaturated and aromatic hydrocarbons also selected types of functionalized organic compounds which play key roles in biogeochemical processes are discussed. For each compound type reactivity and important reaction types with a special focus on mechanisms relevant in biochemical transformations are presented. Bio- and geomacromolecules and their role in the formation of fossil fuels are briefly introduced. Important physico-chemical parameters are discussed in relation to the structural characteristics of the presented compound classes.
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References
- Allred AL (1961) Electronegativity values from thermochemical data. J Inorg Nucl Chem 17: 215–221. ArticleCASGoogle Scholar
- Ballschmiter K, Schäfer W, Buchert H (1987) Isomer-specific identification of PCB congeners in technical mixtures and environmental samples by HRGC-ECD and HRGC-MSD. Fresenius Journal of Anal Chem 326: 253–257. ArticleCASGoogle Scholar
- Ballschmiter K (2003) Pattern and sources of naturally produced organohalogens in the marine environment: biogenic formation of organohalogens. Chemosphere 52: 313–324. ArticlePubMedCASGoogle Scholar
- Boll M, Fuchs G, Heider J (2002) Anaerobic oxidation of aromatic compounds and hydrocarbons. Curr Opin Chem Biol 6: 604–611. ArticlePubMedCASGoogle Scholar
- Brown RJC, Brown RFC (2000) Melting point and molecular symmetry. J Chem Educ 77: Google Scholar
- Buckel W, Golding BT (2006) Radical enzymes in anaerobes. Ann Rev Microbiol 60: 27–49. ArticleCASGoogle Scholar
- Curiale JA, Frolov EB (1998) Occurrence and origin of olefins in crude oils. A critical review. Org Geochem 29: 397–408. ArticleCASGoogle Scholar
- Dahl JE, Liu SG, Carlson RMK (2003a) Isolation and structure of higher diamondoids, nanometer-sized diamond molecules. Science 299: 96–99. ArticlePubMedCASGoogle Scholar
- Dahl JEP, Moldowan JM, Peakman TM, Clardy JC, Lobovsky E, Olmstead MM, May PW, Davis TJ, Steeds JW, Peters KE, Pepper A, Ehkuan A, Carlson RMK (2003b) Isolation and structural proof of the large diamond molecule, cyclohexamantane (C26H30). Angew Chem 115: 2086–2090. ArticleGoogle Scholar
- Dahl JE, Moldowan JM, Peters KE, Claypool GE, Rooney MA, Michael GE, Mello MR, Kohnen ML (1999) Diamondoid hydrocarbons as indicators of natural oil cracking. Nature 399: 54–57. ArticleCASGoogle Scholar
- Boer J, de deBoer K, Boon JP (2000) Polybrominated biphenyls and diphenyl ethers. In The Handbook of Environmental Chemistry, vol 3 Anthropogenic compounds Part K. J. Paasivirta (ed.). Berlin: Springer. pp. 61–96. ChapterGoogle Scholar
- Ficken KJ, Li B, Swain DL, Eglinton G (2000) An n-alkane proxy for the sedimentary input of submerged/floating freshwater aquatic macrophytes. Org Geochem 31: 745–749. ArticleCASGoogle Scholar
- Fiedler H (1996) Sources of PCDD/PCDF and impact on the environment. Chemosphere 32: 55–64. ArticlePubMedCASGoogle Scholar
- Fleming FF (1999) Nitrile-containing natural products. Nat Prod Reports 16: 597–606. ArticleCASGoogle Scholar
- Francke W, Schulz S (1998) pheromones. In: Comprehensive Natural Products Chemistry, vol 8. K Mori (ed.). Oxford: Pergamon, pp. 197–261. Google Scholar
- Gribble GW (1994) The natural production of chlorinated compounds. Environ Sci Technol 28: 310A–319A. ArticleCASGoogle Scholar
- Gribble GW (2000) The natural production of organobromine compounds. Environ Sci Pollut Res Int 7: 37–49. ArticlePubMedCASGoogle Scholar
- Grice K, Alexander R, Kagi RI (2000) Diamondoid hydrocarbon ratios as indicators of biodegradation in Australian crude oils. Org Geochem 31: 67–73. ArticleCASGoogle Scholar
- Hall C, Tharakan P, Hallock J, Cleveland C, Jefferson M (2003) Hydrocarbons and the evolution of human culture. Nature 426: 318–322. ArticlePubMedCASGoogle Scholar
- Hebting Y, Schaeffer P, Behrens A, Adam P, Schmitt G, Schneckenburger P, Bernasconi SM, Albrecht P (2006) Biomarker evidence for a major preservation pathway of sedimentary organic carbon. Science 312: 1627–1631. ArticlePubMedCASGoogle Scholar
- Heider J (2007) Adding handles to unhandy substrates: anaerobic hydrocarbon activation mechanisms. Curr Opin Chem Biol 11: 188–194. ArticlePubMedCASGoogle Scholar
- Hinrichs K-U, Hayes JM, Bach W, Spivack AJ, Hmelo LR, Holm NG, Johnson CG, Sylva SP (2006) Biological formation of ethane and propane in the deep marine subsurface. Proc Natl Acad Sci USA 103: 14684–14689. ArticlePubMedCASGoogle Scholar
- Huc AY (1980) Origin and formation of organic matter in recent sediments and its relation to kerogen. In: Kerogen, Insoluble Organic Matter from Sedimentary Rocks. B Durand (ed.). Paris: Editions Technip, pp. 445–474. Google Scholar
- Leeuw JW, de Largeau C (1993) A review of macromolecular organic compounds that comprise living organisms and their role in kerogen, coal and petroleum formation. In: Organic Geochemistry – Principles and Applications. MH Engel, SA Macko (eds.). New York: Plenum Press, pp. 23–72. Google Scholar
- Lide DR (2002) CRC Handbook of Chemistry and Physics, 83rd edn. 2002–2003. Boca Raton, FL: CRC Press. Google Scholar
- Mango FD (2000) The origin of light hydrocarbons. Geochim Cosmochim Acta 64: 1265–1277. ArticleCASGoogle Scholar
- Marynowski L, Czechowski F, Simoneit BRT (2001) Phenylnaphthalenes and polyphenyls in Palaeozoic source rocks of the Holy Cross Mountains, Poland. Org Geochem 32: 69–85. ArticleCASGoogle Scholar
- McMillen DF, Golden DM (1982) Hydrocarbon bond dissociation energies. Annu Rev Phys Chem 33: 493–532. ArticleCASGoogle Scholar
- Peters KE, Walters CC, Moldowan JM (2005) The Biomarker Guide. Cambridge: Cambridge University Press. Google Scholar
- Portella G, Poater J, Solà M (2005) Assessment of Clar’s aromatic pi-sextet rule by means of PDI, NICS and HOMA indicators of local aromaticity. J Phys Org Chem 18: 785–791. ArticleCASGoogle Scholar
- Rabus R, Wilkes H, Behrends A, Armstroff A, Fischer T, Pierik AJ, Widdel F (2001) Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: Evidence for (1-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism. J Bacteriol 183: 1707–1715. ArticlePubMedCASGoogle Scholar
- Randic M (2003) Aromaticity of polycyclic conjugated hydrocarbons. Chem Rev 103: 3449–3606. Google Scholar
- Schenk HJ, Horsfield B, Krooss B, Schaefer RG, Schwochau K (1997) Kinetics of petroleum formation and cracking. In Petroleum and Basin Evolution. DH Welte, B Horsfield, DR Baker (eds.). Berlin: Springer, pp. 231–269. Google Scholar
- Schneider-Belhaddad F, Kolattukudy P (2000) Solubilization, partial purification, and characterization of a fatty aldehyde decarbonylase from a higher plant, Pisum sativum. Arch Biochem Biophys 377: 341–349. Google Scholar
- Schoell M (1980) The hydrogen and carbon isotopic composition of methane from natural gases of various origins. Geochim Cosmochim Acta 44: 649–661. ArticleCASGoogle Scholar
- Sinninghe Damsté JS, Strous M, Rijpstra WIC, Hopmans EC, Geenevasen JAJ, Duin ACT, van Niftrik LA, van Jetten MSM (2002) Linearly concatenated cyclobutane lipids form a dense bacterial membrane. Nature 419: 708–712. ArticlePubMedGoogle Scholar
- Taylor P, Larter S, Jones M, Dale J, Horstad I (1997) The effect of oil-water-rock partitioning on the occurrence of alkylphenols in petroleum systems. Geochim Cosmochim Acta 61: 1899–1910. ArticleCASGoogle Scholar
- Vandenbroucke M, Largeau C (2007) Kerogen origin, evolution and structure. Org Geochem 38: 719–833. ArticleCASGoogle Scholar
- Yunker MB, MacDonald RW, Vingarzan R, Mitchell RH, Goyette D, Sylvestre S (2002) pahs in the Fraser River basin: a critical appraisal of PAH ratios as indicators of PAH source and composition. Org Geochem 33: 489–515. ArticleCASGoogle Scholar
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Authors and Affiliations
- Helmholtz Centre Potsdam, GFZ German Research Centre for Geosciences, Organic Geochemistry, Potsdam, Germany H. Wilkes
- Institute of Geology and Geochemistry of Petroleum and Coal, RWTH Aachen University, Aachen, Germany J. Schwarzbauer
- H. Wilkes