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  • 1.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation2010In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 17, p. 5882-5887Article in journal (Refereed)
    Abstract [en]

    The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

  • 2.
    Caraballo, Remi
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Phosphine-catalyzed disulfide metathesis2008In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 48, p. 6603-6605Article in journal (Refereed)
    Abstract [en]

    The reaction between disulfides and phosphines generates a reversible disulfide metathesis process.

  • 3.
    Dong, Hai
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Supramolecular Control in Carbohydrate Epimerization: Discovery of a New Anion Host−Guest System2008In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, p. 15270-15271Article in journal (Refereed)
    Abstract [en]

    A new anion-carbohydrate recognition system is described. Pyranosides with axial protons in 1-, 3-, and 5-position proved efficient, forming relatively strong complexes between the anion and the B-face of the carbohydrate. This system could furthermore be used in supramolecular control in Lattrell-Dax epimerization reactions, leading to either activation or deactivation effects.

  • 4.
    Dong, Hai
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Thota, Niranjan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Deng, Lingquan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Control of the ambident reactivity of the nitrite ion2013In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, no 4, p. 648-653Article in journal (Refereed)
    Abstract [en]

    In previous studies, it was reported that a neighbouring equatorial ester group is essential for a good yield of nitrite-mediated triflate inversion, whereas with neighbouring benzyl ether groups or axial ester groups, mixtures are generally produced. In the present study, the origin of this difference was addressed. The ambident reactivity of the nitrite ion has been found to be the cause of the complex product formation observed, which can be controlled by a neighbouring equatorial ester group. Both N-attack and O-attack occur in the absence of the ester group, whereas O-attack is favoured in its presence. A neighbouring group assistance mechanism is proposed, in addition to steric effects, based on secondary interactions between the neighbouring ester group and the incoming nucleophile. High-level quantum mechanical calculations were carried out in order to delineate this effect. The theoretical results are in excellent agreement with experiments, and suggest a catalytic role for the neighbouring equatorial ester group.

  • 5.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Green Propellants2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    To enable future environmentally friendly access to space by means of solid rocket propulsion a viable replacement to the hazardous ammonium perchlorate oxidizer is needed. Ammonium dinitramide (ADN) is one of few such compounds currently known. Unfortunately compatibility issues with many polymer binder systems and unexplained solid-state behavior have thus far hampered the development of ADN-based propellants.

    Chapters one, two and three offer a general introduction to the thesis, and into relevant aspects of quantum chemistry and polymer chemistry.

    Chapter four of this thesis presents extensive quantum chemical and spectroscopic studies that explain much of ADN’s anomalous reactivity, solid-state behavior and thermal stability. Polarization of surface dinitramide anions has been identified as the main reason for the decreased stability of solid ADN, and theoretical models have been developed to explain and predict the solid-state stability of general dinitramide salts. Experimental decomposition characteristics for ADN, such as activation energy and decomposition products, have been explained for different physical conditions. The reactivity of ADN towards many chemical groups is explained by ammonium-mediated conjugate addition reactions. It is predicted that ADN can be stabilized by changing the surface chemistry with additives, for example by using hydrogen bond donors, and by trapping radical intermediates using suitable amine-functionalities.

    Chapter five presents several conceptual green energetic materials (GEMs), including different pentazolate derivatives, which have been subjected to thorough theoretical studies. One of these, trinitramide (TNA), has been synthesized and characterized by vibrational and nuclear magnetic resonance spectroscopy.

    Finally, chapter six covers the synthesis of several polymeric materials based on polyoxetanes, which have been tested for compatibility with ADN. Successful formation of polymer matrices based on the ADN-compatible polyglycidyl azide polymer (GAP) has been demonstrated using a novel type of macromolecular curing agent. In light of these results further work towards ADN-propellants is strongly encouraged.

  • 6.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Dinitraminic acid (HDN) isomerization and self-decomposition revisited2008In: Chemical Physics, ISSN 0301-0104, E-ISSN 1873-4421, Vol. 348, no 1-3, p. 53-60Article in journal (Refereed)
    Abstract [en]

    Density functional theory (DFT) and the ab initio based CBS-QB3 method have been used to study possible decomposition pathways of dinitraminic acid HN(NO2)(2) (HDN) in gas-phase. The proton transfer isomer of HDN, O2NNN(O)OH, and its conformers can be formed and converted into each other through intra- and intermolecular proton transfer. The latter has been shown to proceed substantially faster via double proton transfer. The main mechanism for HDN decomposition is found to be initiated by a dissociation reaction, splitting of nitrogen dioxide from either HDN or the HDN isomer. This reaction has an activation enthalpy of 36.5 kcal/mol at the CBS-QB3 level, which is in good agreement with experimental estimates of the decomposition barrier.

  • 7.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Kinetic Stability and Propellant Performance of Green Energetic Materials2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, p. 6590-6600Article in journal (Refereed)
    Abstract [en]

    A thorough theoretical investigation of four promising green energetic materials is presented. The kinetic stability of the dinitramide, trinitrogen dioxide, pentazole, and oxopentazole anions has been evaluated in the gas phase and in solution by using high-level ab initio and DFT calculations. Theoretical UV spectra, solid-state heats of formation, density, as well as propellant performance for the corresponding ammonium salts are reported. All calculated properties for dinitramide are in excellent agreement with experimental data. The stability of the trinitrogen dioxide anion is deemed sufficient to enable synthesis at low temperature, with a barrier for decomposition of approximately 27.5 kcal mol(-1) in solution. Oxopentazolate is expected to be approximately 1200 times more stable than pentazolate in solution, with a barrier exceeding 30 kcal mol(-1), which should enable handling at room temperature. All compounds are predicted to provide high specific impulses when combined with aluminum fuel and a polymeric binder, and rival or surpass the performance of a corresponding ammonium perchlorate based propellant. The investigated substances are also excellent monopropellant candidates. Further study and attempted synthesis of these materials is merited.

  • 8.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Novel 1,3-dipolar cycloadditions of dinitraminic acid: Implications for the chemical stability of ammonium dinitramide2008In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 112, no 11, p. 2456-2463Article in journal (Refereed)
    Abstract [en]

    Density functional theory at the B3LYP/6-31+G(d,p) level and ab initio calculations at the CBS-QB3 level have been used to analyze 1,3 dipolar cycloaddition reactions of dinitraminic acid (HDN) and its proton transfer isomer (HO(O)NNNO2). It is shown that the nitro group of HDN and the -N-N = O functionality of the isomer react readily with carbon-carbon double bonds. Cycloadditions of HDN are compared with the corresponding reactions with azides and nitrile oxides as 1,3 dipoles. It is shown that the reactivities of HDN and its proton transfer isomer decrease with increasing electron withdrawing power of the substituents adjacent to the carbon-carbon double bond. In contrast, for azides and nitrile oxides, the highest reactivity is obtained with dipolarophiles with strongly electron withdrawing substituents. The observed reactivity trends allow for the design of unsaturated compounds that are highly reactive toward azides and chemically inert toward dinitramides. This may be of relevance for the development of binder materials for ammonium dinitramide based propellants.

  • 9.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    On the Anomalous Decomposition and Reactivity of Ammonium and Potassium Dinitramide2010In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 114, no 8, p. 2845-2854Article in journal (Refereed)
    Abstract [en]

    Mechanistic pathways for the thermal decomposition of the solid-state energetic oxidizers ammonium dinitramide (ADN) and potassium dinitramide (KDN) have been deciphered by carefully considering previously performed experimental studies and using state of the art quantum chemical modeling of molecular clusters. Decomposition is governed by surface chemical processes, involving polarized (twisted) dinitramide anions of reduced stability. Under atmospheric and low-pressure conditions, the rate-determining step for the decomposition of these dinitramide salts is the dissociation into NO, and NNO2- radicals. The activation barriers for these steps are estimated to be 30 and 36 kcal/mol for ADN and KDN, respectively. The known stabilizing effect of water is explained by its hydrogen bonding ability, which counteracts polarization of surface dinitramides. The reactivity of ADN toward Various chemical environments is likely explained through metastable decomposition radical intermediates. Donation of hydrogen bonds, antioxidant character, and basicity are properties believed to correlate with a compound's ability to act as a stabilizer for dinitramide salts.

  • 10.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE).
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Centres, Centre of Molecular Devices, CMD.
    Solid-state modeling of dinitramide decomposition2009In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Article in journal (Other academic)
  • 11.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    The anomalous solid state decomposition of ammonium dinitramide: a matter of surface polarization2009In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 20, p. 2896-2898Article in journal (Refereed)
    Abstract [en]

    Polarized dinitramide anions on the surface of solid ammonium dinitramide (ADN) have a decomposition barrier that is reduced by 16 kcal mol(-1) and explain the anomalous solid state decomposition of ADN.

  • 12.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Dvinskikh, Sergey V.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Furo, Istvan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Experimental Detection of Trinitramide, N(NO2)(3)2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 5, p. 1145-1148Article in journal (Refereed)
    Abstract [en]

    Propeller propellant: The largest nitrogen oxide to date, trinitramide (TNA), has been prepared following extensive quantum chemical studies in which its kinetic stability and several physical properties were estimated. TNA was detected using IR and NMR spectroscopy. The compound is highly energetic and shows promise for cryogenic propulsion and as a reagent in high-energy-density material research.

  • 13.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Malmström, Eva
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Eldsäter, Carina
    Design of an Ammonium Dinitramide Compatible Polymer MatrixManuscript (preprint) (Other academic)
  • 14.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Malmström, Eva
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Eldsäter, Carina
    Design of an Ammonium Dinitramide Compatible Polymer Matrix2011In: Journal of Applied Polymer Science, ISSN 0021-8995, E-ISSN 1097-4628, Vol. 122, no 1, p. 1-11Article in journal (Refereed)
    Abstract [en]

    To enable future environmentally friendly access to space by means of solid rocket propulsion a viable replacement to the toxic ammonium perchlorate (AP) oxidizer is needed. Ammonium dinitramide (ADN) holds great promise as a green replacement. Unfortunately compatibility issues with many polymer binder systems have hampered the development of ADN-based formulations. Herein we present proof-of-concept of a polymer cure system based on hyperbranched copolymers of 3-ethyl-3-(hydroxymethyl)oxetane (TMPO) and tetrahydrofuran (THF). The partly alkyne-functionalized macromolecules were synthesized in a one-pot procedure. TMPO and THF are found to polymerize in exact ratios, indicating a kinetically controlled buildup of nonrandom composition copolymers. Several of the materials show excellent compatibility with ADN, and rapid curing of the energetic polyglycidyl azide polymer (GAP) have been demonstrated through 1,3-dipolar cycloaddition at 75 degrees C.

  • 15.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Trinchero, Adriana
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Envisioning New High Energy Density Materials: Stability, Detection and Performance2010In: 41st International  Annual Conference of  ICT (Energetic Materials) : , 2010, p. 9/1-9/11Conference paper (Other academic)
    Abstract [en]

    There is great need for new environmentally friendly energetic materials. One promising oxidizer currently under investigation for numerous applications is ammonium dinitramide (ADN, NH4N(NO2)2). After deciphering the thermal decomposition behavior of this salt theoretically, we have sought to find other all-nitrogen-oxygen compounds with similar advantageous properties. By considering electronic and structural characteristics related to the dinitramide, we have investigated a number of promising energetic anions using high-level density functional theory and ab initio methods.   Theoretical kinetic stabilities, UV-spectra, solid-state heats of formation, densities, as well as propellant performances of the corresponding ammonium salts with aluminum fuel are reported. The potential for significant performance gains is seen by comparison to standard ammonium perchlorate (AP) and ADN-formulations. Reasonable stabilities and straightforward detection at room temperature should encourage attempted synthesis of several of the investigated materials.

  • 16.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Tyrode, Eric
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Surface Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Johnson, Magnus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Corrosion Science.
    The Molecular Surface Structure of Ammonium and Potassium Dinitramide: A Vibrational Sum Frequency Spectroscopy and Quantum Chemical Study2011In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 115, no 21, p. 10588-10596Article in journal (Refereed)
    Abstract [en]

    Vibrational sum frequency spectroscopy (VSFS) and quantum chemical modeling have been employed to investigate the molecular surface structure of ammonium and potassium dinitramide (ADN and KDN) crystals. Identification of key vibrational modes was made possible by performing density functional theory calculations of molecular clusters. The surface of KDN was found to be partly covered with a thin layer of the decomposition product KNO3, which due to its low thickness was not detectable by infrared and Raman spectroscopy. In contrast, ADN exhibited an extremely inhomogeneous surface, on which polarized dinitramide anions were present, possibly together with a thin layer of NH4NO3. The intertwined use of theoretical and experimental tools proved indispensable in the analysis of these complex surfaces. The experimental verification of polarized and destabilized dinitramide anions stresses the importance of designing surface-active polymer support, stabilizers, and/or coating agents, in order to enable environmentally friendly ADN-based solid-rocket propulsion.

  • 17.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.
    Westlund, Robert
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Eldsäter, Carina
    Malmström, Eva
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Tri-Block Copolymers of Polyethylene Glycol and Hyperbranched Poly-3-ethyl-3-(hydroxymethyl)oxetane Through Cationic Ring Opening Polymerization2009In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 47, no 22, p. 6191-6200Article in journal (Refereed)
    Abstract [en]

    Tri-block copolymers of linear poly(ethylene glycol) (PEG) and hyperbranched poly-3-ethyl-3-(hydroxymethyl)oxetane (poly-TMPO) are reported. The novel dumb-bell shaped polyethers were synthesized in bulk with cationic ring-opening polymerization utilizing BF3OEt2 as initiator, via drop-wise addition of the oxetane monomer. The thermal properties of the materials were successfully tuned by varying the amount of poly-TMPO attached to the PEG-chains, ranging from a melting point of 54 degrees C and a degree of crystallinity of 76% for pure PEG, to a melting point of 35 degrees C and a degree of crystallinity of 12% for the polyether copolymer having an average of 14 TMPO units per PEG chain. The materials are of relatively low polydispersity, with M-n/M-w ranging from 1.2 to 1.4. The materials have been evaluated for usage with the energetic oxidizer ammonium dinitramide.

  • 18.
    Rahm, Martin
    et al.
    KTH, School of Chemical Science and Engineering (CHE).
    Westlund, Robert
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Malmström, Eva
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    POLY 41-Dumbbell shaped tri-block copolymers of hyperbranched poly-3-ethyl-3-(hydroxymethyl)oxetane and polyethylene glycol through cationic ring opening polymerization2009In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Article in journal (Other academic)
  • 19. Ren, Bo
    et al.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. Cornell Univiversity, USA .
    Zhang, Xiaoling
    Zhou, Yixuan
    Dong, Hai
    Regioselective Acetylation of Diols and Polyols by Acetate Catalysis: Mechanism and Application2014In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 17, p. 8134-8142Article in journal (Refereed)
    Abstract [en]

    We propose a principle for H-bonding activation in acylation of hydroxyl groups, where the acylation is activated by the formation of hydrogen bonds between hydroxyl groups and anions. With the guidance of this principle, we demonstrate a method for the selective acylation of carbohydrates. By this method, diols and polyols are regioselectively acetylated in high yields under mild conditions using catalytic amounts of acetate. In comparison to other methods involving reagents such as organotin, organoboron, organosilicon, organobase, and metal salts, this method is more environmentally friendly, convenient, and efficient and is also associated with higher regioselectivity. We have performed a thorough quantum chemical study to decipher the mechanism, which suggests that acetate first forms a dual H-bond complex with a diol, which enables subsequent monoacylation by acetic anhydride under mild conditions. The regioselectivity appears to originate from the inherent structure of the diols and polyols and their specific interactions with the coordinating acetate catalyst.

1 - 19 of 19
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