Alt, J. C., Garrido, C. J., Shanks, W. C. III, Turchyn, A., Padrón-Navarta, J. A., Sánchez-Vizcaíno, V. L., Goméz Pugnaire, M. T. and Marchesi, C. (2012a) Recycling of water, carbon, and sulfur during subduction of serpentinites: a stable isotope study of Cerro del Almirez, Spain. Earth Planet. Sci. Lett. 327–328, 50–60.
Alt, J. C., Shanks, W. C. III, Crispini, L., Gaggero, L., Schwarzenbach, E. M., Früh-Green, G. L. and Bernasconi, S. M. (2012b) Uptake of carbon and sulfur during seafloor serpentinization and the effects of subduction metamorphism in Ligurian peridotites. Chem. Geol. 322–323, 268–277.
Alt, J. C., Schwarzenbach, E. M., Früh-Green, G. L., Shanks, W. C., Bernasconi, S. M., Garrido, C. J., Crispini, L., Gaggero, L., Padrón-Navarta, J. A. and Marchesi, C. (2013) The role of serpentinites in cycling of carbon and sulfur: seafloor serpentinization and subduction metamorphism. Lithos 178, 40–54.
Amend, J. P. and Shock, E. L. (2001) Energetics of overall metabolic reactions of thermophilic and hyperthemophilic Archaea and Bacteria. FEMS Microbiol. Rev. 25, 175–243.
Anslyn, E. and Dougherty, D. (2005) Modern Physical Organic Chemistry. Sausalito, CA: University Science Books.
Antal, M. J., Carlsson, M., Xu, X. and Anderson, D. G. M. (1998) Mechanism and kinetics of the acid-catalyzed dehydration of 1- and 2-propanol in hot compressed liquid water Ind. Eng. Chem. Res. 37, 3820–3829.
Bada, J. L., Wang, X. S. and Hamilton, H. (1999) Preservation of key biomolecules in the fossil record: current knowledge and future challenges. Philos. Trans. R. Soc. Lond. B Biol. Sci. 354, 77–87.
Berner, R. A. (2006) Geological nitrogen cycle and atmospheric N2 over Phanerozoic time. Geology 34, 413–415.
Bianchi, T. S. (2011) The role of terrestrially derived organic carbon in the coastal ocean: a changing paradigm and the priming effect. Proc. Natl Acad. Sci. USA 108, 19473–19481.
Bockisch, C., Lorance, E. D., Hartnett, H. E., Shock, E. L. and Gould I. R. (2018) Kinetics and mechanisms of dehydration of secondary alcohols under hydrothermal conditions. ACS Earth Space Chem. 2, 821–832.
Boudou, J. P., Schimmelmann, A., Ader, M., Mastalerz, M., Sebilo, M. and Gengembre, L. (2008) Organic nitrogen chemistry during low-grade metamorphism. Geochim. Cosmochim. Acta 72, 1199–1221.
Brown, H. C. and Ramachandran, P. V. (1996) Sixty years of hydride reductions. In Abdel-Magid, A. F. (ed.). Reductions in Organic Synthesis: Recent Advances and Practical Applications. ACS Symposium Series, Vol. 641, pp. 1–30, Washington, DC: American Chemical Society.
Cannizzaro S. (1853) Über den der Benzoësaüre entsprechenden Alkohol. Justus Liebigs Ann. Chem. 88, 129–130.
Clift, P. D. (2017) A revised budget for Cenozoic sedimentary carbon subduction. Rev. Geophys. 55, 97–125.
Cottrell, E. and Kelley, K. A. (2011) The oxidation state of Fe in MORB glasses and the oxygen fugacity of the upper mantle. Earth Planet. Sci. Lett. 305, 270–282.
Cox, J. S. and Seward, T. M. (2007) The hydrothermal reaction kinetics of aspartic acid. Geochim. Cosmochim. Acta 71, 797–820.
Cumberland, S. A., Douglas, G., Grice, K., and Moreau, J. W. (2016) Uranium mobility in organic matter-rich sediments: a review of geological and geochemical processes. Earth Sci. Rev. 159, 160–185.
Dale, W. M. and Davies, J. V. (1950) Deamination of aqueous solutions of l-serine by X-radiation. Nature 166, 1121.
Dick, J. M., LaRowe, D. E. and Helgeson, H. C. (2006) Temperature, pressure, and electrochemical constraints on protein speciation: group additivity calculation of the standard molal thermodynamic properties of ionized unfolded proteins, Biogeosciences 3, 311–336.
Dummer, N. F., Bawaked, S., Hayward, J., Jenkins, R. and Hutchings, G. J. (2010) Oxidative dehydrogenation of cyclohexane and cyclohexene over supported gold, palladium and gold–palladium catalysts. Catal. Today 154, 2–6.
El-Deeb, I. Y., Tian, M., Funakoshi, T., Matsubara, R. and Hayashi, M. (2017) Conversion of cyclohexanones to alkyl aryl ethers by using a Pd/C-ethylene system. Eur. J. Org. Chem. 2017, 409–413.
Fecteau, K. M., Gould, I. R., Glein, C. R., Williams, L. B., Hartnett, H. E. and Shock, E. L. (2019) Production of carboxylic acids from aldehydes under hydrothermal conditions: a kinetic study of benzaldehyde. ACS Earth Space Chem. 3, 170–191.
Friesen, J. B. and Schretzman, R. (2011) Dehydration of 2-methyl-1-cyclohexanol: new findings from a popular undergraduate laboratory experiment. J. Chem. Educ. 88, 1141–1147.
Galloway, J. N., Dentener, F. J., Capone, D. G., Boyer, E. W., Howarth, R. W., Seitzinger, S. P., Asner, G. P., Cleveland, C. C., Green, P. A., Holland, E. A. Karl, D. M., Michaels, A. F., Porter, J. H., Townsend, A. R. and Vörösmarty C. J. (2004) Nitrogen cycles: past, present, and future. Biogeochemistry 70, 153–226.
Garrett, E. R. and Tsau, J. (1972) Solvolyses of cytosine and cytidine. J. Pharm. Sci. 61, 1052–1061.
Gize, A. P. (1999) Organic alteration in hydrothermal sulfide ore deposits. Econ. Geol. 94, 967–979.
Glein, C., Gould, I., Lorance, E., Hartnett, H. and Shock, E. (2019) Mechanisms of decarboxylation of phenylacetic acids and their sodium salts in water at high temperature and pressure. Geochim. Cosmochim. Acta (submitted).
Gordon, A. J. and Ford, R. A. (1972) Chemist’s Companion: A Handbook of Practical Data, Techniques, and References. New York: Wiley.
Greenwood, P. F., Brocks, J. J., Grice, K., Schwark, L., Jaraula, C. M. B., Dick, J. M. and Evans, K. A. (2013) Organic geochemistry and mineralogy. I. Characterisation of organic matter associated with metal deposits. Ore Geol. Rev. 50, 1–27.
Hammett, L. P. (1935) Some relations between reaction rates and equilibrium constants. Chem. Rev. 17, 125–136.
Hedges, J. I. (1992) Global biogeochemical cycles: progress and problems. Mar. Chem. 39, 67–93.
Heinemann, H., Mills, G. A., Hattman, J. B. and Kirsch, F. W. (1953) Houdriforming reactions: studies with pure hydrocarbons. Ind. Eng. Chem. 45, 130–134.
Helgeson, H. C., Knox, A. M., Owens, C. E. and Shock, E. L. (1993) Petroleum, oil field waters and authigenic mineral assemblages: are they in metastable equilibrium in hydrocarbon reservoirs? Geochim. Cosmochim. Acta 57, 3295–3339.
Helgeson, H. C., Richard, L., McKenzie, W. F., Norton, D. L. and Schmitt, A. (2009) A chemical and thermodynamic model of oil generation in hydrocarbon source rocks. Geochim. Cosmochim. Acta 73, 594–695.
Hietala, D. C. and Savage, P. E. (2015) Reaction pathways and kinetics of cholesterol in high-temperature water. Chem. Eng. J. 265, 129–137.
House, H. O. (1972) Modern Synthetic Reactions, 2nd edn. New York: W. A. Benjamin.
Hu, S., Evans, K., Craw, D., Rempel, K., Bourdet, J., Dick, J. and Grice, K. (2015) Raman characterization of carbonaceous material in the Macraes orogenic gold deposit and metasedimentary host rocks, New Zealand. Ore Geol. Rev. 70, 80–95.
Hu, S.-Y., Evans, K., Craw D., Rempel, K. and Grice, K. (2017) Resolving the role of carbonaceous material in gold precipitation in metasediment-hosted orogenic gold deposits. Geology 45, 167–170.
Huang, F., Daniel, I., Cardon, H., Montagnac, G. and Sverjensky, D. A. (2017) Immiscible hydrocarbon fluids in the deep carbon cycle. Nat. Commun. 8, 15798.
Ikushima, Y., Hatakeda, K., Sato, O., Yokoyama, T. and Arai, M. (2001) Structure and base catalysis of supercritical water in the noncatalytic benzaldehyde disproportionation using water at high temperatures and pressures. Angew. Chem., Int. Ed. 40, 210–213.
Katritzky, A. R., Balasubramanian, M. and Siskin, M. (1990a) Aqueous high-temperature chemistry of carbo- and heterocycles. 2. Monosubstituted benzenes: benzyl alcohol, benzaldehyde and benzoic acid. Energy Fuels 4, 499–505.
Katritzky, A. R., Luxem, F. J. and Siskin, M. (1990b) Aqueous high-temperature chemistry of carbo- and heterocycles. 5. Monosubstituted benzenes with a two carbon atom side chain oxygenated at the β-position. Energy Fuels 4, 514–517.
Katritzky, A. R., Nichols, D. A., Siskin, M., Murugan, R. and Balasubramanian, M. (2001) Reactions in high-temperature aqueous media. Chem. Rev. 101, 837–892.
Kelemen, P. B. and Manning, C. E. (2015) Reevaluating carbon flux in subduction zones, what goes down, mostly comes up. Proc. Natl Acad. Sci. USA 112, 3997–4006.
Krumrei, T. V., Pernicka, E., Kaliwoda, M. and Markl, G. (2007) Volatiles in a peralkaline system: abiogenic hydrocarbons and F–Cl–Br systematics in the naujaite of the Ilímaussaq intrusion, South Greenland. Lithos 95, 298–314.
Kuhlmann, B., Arnett, E. M. and Siskin, M. (1994) Classical organic reactions in pure superheated water. J. Org. Chem. 59, 3098–3101.
Lammers, L. N., Brown, Jr., G. E., Bird, D. K., Thomas, R. B., Johnson, N. C., Rosenbauer, R. J. and Maher, K. (2015) Sedimentary reservoir oxidation during geologic CO2 sequestration. Geochim. Cosmochim. Acta 155, 30–46.
Mancinelli, R. L. and McKay, C. P. (1988) The evolution of nitrogen cycling. Orig. Life Evol. Biosph. 18, 311–325.
Manning, C. E., Shock, E. L. and Sverjensky, D. A. (2013) The chemistry of carbon in aqueous fluids at crustal and upper-mantle conditions: experimental and theoretical constraints. Rev. Mineral. Geochem. 75, 109–148.
Mattioli, G. S. and Wood, B. J. (1986) Upper mantle oxygen fugacity recorded by spinel lherzolites. Nature 322, 626–628.
Matsuo, J. and Aizawa, Y. (2005) One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions. Tetrahedron Lett. 46, 407–410.
McCollom, T. M. and Seewald, J. S. (2007) Abiotic synthesis of organic compounds in deep-sea hydrothermal environments. Chem. Rev. 107, 382–401.
McDermott, J. M., Seewald, J. S., German, C. R. and Sylva, S. P. (2015) Pathways for abiotic organic synthesis at submarine hydrothermal fields. Proc. Natl Acad. Sci. USA 112, 7668–7672.
McDermott, J. M., Sylva, S. P., Ono, S., German, C. R. and Seewald, J. S. (2018) Geochemistry of fluids from Earth’s deepest ridge-crest hot-springs: Piccard hydrothermal field, Mid-Cayman Rise. Geochim. Cosmochim. Acta 228, 95–118.
Monera, O. D., Chang, M. K. and Means, G. E. (1989) Deamination of n-octylamine in aqueous solution: the substitution/elimination ratio is not altered by a change of 108 in hydroxide ion concentration. J. Org. Chem. 54, 5424–5426.
Nagai, Y., Matubayasi, N. and Nakahara, M. (2004) Noncatalytic disproportionation and decarbonylation reactions of benzaldehyde in supercritical water. Chem. Lett. 33, 622–623.
Nivin, V. A. (2011) Variations in the composition and origin of hydrocarbon gases from inclusions in minerals of the Khibiny and Lovozero Plutons, Kola Peninsula, Russia. Geol. Ore Deposits 53, 699–707.
O’Neill, H. St. C. and Wall, V. J. (1987) The olivine–orthopyroxene–spinel oxygen geobarometer, the nickel precipitation curve, and the oxygen fugacity of the Earth’s upper mantle. J. Petrol. 26, 1169–1191.
Palmer, D. A. and Drummond, S. E. (1986) Thermal decarboxylation of acetate. Part I. The kinetics and mechanism of reaction in aqueous solution. Geochim. Cosmochim. Acta 50, 813–823.
Panizza, M., Resini, C., Busca, G., Fernández López, E. and Sánchez Escribano, V. (2003) A study of the oxidative dehydrogenation of cyclohexane over oxide catalysts. Catal. Lett. 89, 199–205.
Pizzarello S. and Shock, E. (2010) The organic composition of carbonaceous meteorites: the evolutionary story ahead of biochemistry. In Deamer, D. and Shostak, J. (eds.). The Origins of Life, pp. 89–107, Cold Spring Harbor, NY: Cold Spring Harbor Press.
Plyasunov, A. V. and Shock, E. L. (2001) Correlation strategy for determining the parameters of the revised Helgeson–Kirkham–Flowers model for aqueous nonelectrolytes. Geochim. Cosmochim. Acta 65, 3879–3900.
Potter, J., Salvi, S. and Longstaffe, F. J. (2013) Abiogenic hydrocarbon isotopic signatures in granitic rocks: identifying pathways of formation. Lithos 182–183, 114–124.
Price, L. C. and DeWitt, E. (2001) Evidence and characteristics of hydrolytic disproportionation of organic matter during metasomatic processes. Geochim. Cosmochim. Acta 65, 3791–3826.
Robinson, K. J., Gould, I. R., Fecteau, K. M., Hartnett, H. E., Williams, L. B. and Shock, E. L. (2019) Deamination reaction mechanisms of protonated amines under hydrothermal conditions. Geochim. Cosmochim. Acta 244, 113–128.
Romero, A., Santos, A., Escrig, D. and Simon, E. (2011) Comparative dehydrogenation of cyclohexanol and cyclohexanone with commercial copper catalysts: catalytic activity and impurities formed. Appl. Catal. A 392, 19–27.
Rylander, P. N. (1973) Organic Synthesis with Noble Metal Catalysts. New York: Academic Press.
Salvi, S. and Williams-Jones, A. E. (1997) Fischer–Tropsch synthesis of hydrocarbons during sub-solidus alteration of the Strange Lake peralkaline granite, Quebec/Labrador, Canada. Geochim. Cosmochim. Acta 61, 83–99.
Salvi, S. and Williams-Jones, A. E. (2006) Alteration, HFSE mineralization and hydrocarbon formation in peralkaline igneous systems: insights from the Strange Lake Pluton, Canada. Lithos 91, 19–34.
Sawada, Y., Sampei Y., Hada, O. and Taguchi, S. (2008) Thermal degradation and polymerization of carbonaceous materials in a metapelite–granitoid magma system in the Ryoke metamorphic belt, SW Japan. J. Asian Earth Sci. 33, 91–105.
Seewald, J. S. (2001) Aqueous geochemistry of low molecular weight hydrocarbons at elevated temperatures and pressures: constraints from mineral buffered laboratory experiments. Geochim. Cosmochim. Acta 65, 1641–1664.
Seewald, J. S. (2003) Organic–inorganic interactions in petroleum-producing sedimentary basins. Nature 426, 327–333.
Seewald, J. S. (2017) Laboratory simulations of organic geochemical processes at elevated temperatures. In White, W. M. (ed.). Encyclopedia of Geochemistry: Encyclopedia of Earth Science Series, pp. 789–792, New York: Springer International Publishing.
Shadyro, O. I., Sosnovskaya, A. A. and Vrublevskaya, O. N. (2003) C–N bond cleavage reactions on the radiolysis of amino-containing organic compounds and their derivatives in aqueous solutions. Int. J. Radiat. Biol. 79, 269–279.
Shipp, J., Gould, I. R., Herckes, P., Shock, E. L., Williams, L. B. and Hartnett, H. E. (2013) Organic functional group transformations in water at elevated temperature and pressure: reversibility, reactivity, and mechanisms. Geochim. Cosmochim. Acta 104, 194–209.
Shipp, J. A., Gould, I. R., Shock, E. L., Williams, L. B. and Hartnett, H. E. (2014) Sphalerite is a geochemical catalyst for carbon–hydrogen bond activation. Proc. Natl Acad. Sci. USA 111, 11642–11645.
Shock, E. L. (1990) Geochemical constraints on the origin of organic compounds in hydrothermal systems. Orig. Evol. Life Biosph. 20, 331–367.
Shock, E. L. (1992) Chemical environments of submarine hydrothermal systems. Orig. Evol. Life Biosph. 22, 67–107.
Shock, E. L. (1993) Hydrothermal dehydration of aqueous organic compounds. Geochim. Cosmochim. Acta 57, 3341–3349.
Shock, E. L. (1994) Application of thermodynamic calculations to geochemical processes involving organic acids. In Pittman, E. D. and Lewan M. D. (eds.). Organic Acids in Geological Processes, pp. 270–318, Berlin: Springer.
Shock, E. L. (1995) Organic acids in hydrothermal solutions: standard molal thermodynamic properties of carboxylic acids and estimates of dissociation constants at high temperatures and pressures. Am. J. Sci. 295, 496–580.
Shock, E. L. and Helgeson, H. C. (1990) Calculation of the thermodynamic and transport properties of aqueous species at high pressures and temperatures: standard partial molal properties of organic species. Geochim. Cosmochim. Acta 54, 915–945.
Shock, E. L., Helgeson, H. C. and Sverjensky, D. A. (1989) Calculation of the thermodynamic and transport properties of aqueous species at high pressures and temperatures: standard partial molal properties of inorganic neutral species. Geochim. Cosmochim. Acta 53, 2157–2183.
Shock, E. L., Oelkers, E. H., Johnson, J. W., Sverjensky, D. A. and Helgeson, H. C. (1992) Calculation of the thermodynamic properties of aqueous species at high pressures and temperatures: effective electrostatic radii, dissociation constants, and standard partial molal properties to 1000°C and 5 kb. J. Chem. Soc. Faraday Trans. 88, 803–826.
Shock, E. L., Sassani, D. C., Willis, M. and Sverjensky, D. A. (1997) Inorganic species in geologic fluids: correlations among standard molal thermodynamic properties of aqueous ions and hydroxide complexes. Geochim. Cosmochim. Acta 61, 907–950.
Shock, E. L., Canovas, P., Yang, Z., Boyer, G., Johnson, K., Robinson, K., Fecteau, K., Windman, T. and Cox, A. (2013) Thermodynamics of organic transformations in hydrothermal fluids. Rev. Mineral. Geochem. 76, 311–350.
Streitwieser, A., Heathcock, C. H. and Kosower, E. M. (1995) Introduction to Organic Chemistry, 4th edn. Upper Saddle River, NJ: Prentice-Hall.
Swain, C. G., Powell, A. L., Sheppard, W. A. and Morgan, C. R. (1979) Mechanism of the Cannizzaro reaction. J. Am. Chem. Soc. 101, 3576–3583.
Taran, Y. A. and Giggenbach, W. F. (2003) Geochemistry of light hydrocarbons in subduction-related volcanic and hydrothermal fluids. In Simmons, S. F. and Graham, I. (eds.). Volcanic, Geothermal, and Ore-Forming Fluids; Rulers and Witnesses of Processes within the Earth, pp. 61–74, Littleton, CO: Society of Economic Geologists.
Tassi, F., Venturi, S., Cabassi, J., Capecchiacci, F., Nisi, B. and Vaselli, O. (2015) Volatile organic compounds (VOCs) in soil gases from Solfatara crater (Campi Flegrei, southern Italy): geogenic source(s) vs. biogeochemical processes. Appl. Geochem. 56, 37–49.
Tsao, C. C., Zhou, Y., Liu, X. and Houser, T. J. (1992) Reactions of supercritical water with benzaldehyde, benzylidenebenzylamine, benzyl alcohol, and benzoic acid. J. Supercrit. Fluids 5, 107–113.
Venturi, S., Tassi, F., Gould, I. R., Shock, E. L., Hartnett, H. E., Lorance, E. D., Bockisch, C., Fecteau, K. M., Capecchiacci, F. and Vaselli, O. (2017) Mineral-assisted production of benzene under hydrothermal conditions: insights from experimental studies on C6 cyclic hydrocarbons. J. Volcanol. Geothermal Res. 346, 21–27.
Wang, D. T., Reeves, E. P., McDermott, J. M., Seewald, J. S. and Ono, S. (2018) Clumped isotopologue constraints on the origin of methane at seafloor hot springs. Geochim. Cosmochim. Acta 223, 141–158.
Wang, S. and Hu, A. (2016) Comparative study of spontaneous deamination of adenine and cytosine in unbuffered aqueous solution at room temperature. Chem. Phys. Lett. 653, 207–211.
White, E. H. and Scherrer, H. (1961) The triazene method for the deamination of aliphatic amines. Tetrahedron Lett. 2, 758–762.
Wilberg, K. B. (1965) Oxidation by chromic acid and chromyl compounds. In Wilberg, K. B. (ed.). Oxidation in Organic Chemistry, pp. 69–184, New York: Academic Press.
Xu, X. and Antal, M. J. (1994) Kinetics and mechanism of isobutene formation from t-butanol in hot liquid water. AIChE J. 40, 1524–1534.
Xu, X., Antal, M. J. and Anderson D. G. M. (1997) Mechanism and temperature-dependent kinetics of the dehydration of tert-butyl alcohol in hot compressed liquid water. Ind. Eng. Chem. Res. 36, 23–41.
Xu, X., De Almeida, C. P. and Antal, M. J., Jr. (1991) Mechanism and kinetics of the acid-catalyzed formation of ethene and diethyl ether from ethanol in supercritical water. Ind. Eng. Chem. Res. 30, 1478–1485.
Yang, Z., Gould, I. R., Williams, L. B., Hartnett, H. E. and Shock, E. L. (2012) The central role of ketones in reversible and irreversible hydrothermal organic functional group transformations. Geochim. Cosmochim. Acta 98, 48–65.
Yang, Z., Hartnett, H. E., Shock, E. L. and Gould, I. R. (2015) Organic oxidations using geomimicry. J. Org. Chem. 80, 12159–12165.
Yang, Z., Williams, L. B., Hartnett, H. E., Gould, I. R. and Shock, E. L. (2018) Effects of iron-containing minerals on hydrothermal reactions of ketones. Geochim. Cosmochim. Acta 223, 107–126.
Zweifel, G. S. and Nantz, M. H. (2006) Modern Organic Synthesis: An Introduction. New York: W. H. Freeman.