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  1. Ajay R, JafarAbdulla MU, Sivakumar JS, Baburajan K, Rakshagan V, Eyeswarya J
    J Contemp Dent Pract, 2023 Aug 01;24(8):521-544.
    PMID: 38193174 DOI: 10.5005/jp-journals-10024-3514
    AIM: The present systematic review aimed to report the studies concerning the primers in improving bond strength and identifying pertinent primers for a particular dental alloy by adhering to PRISMA precepts.

    MATERIALS AND METHODS: PubMed and Semantic Scholar databases were scoured for articles using 10 search terms. In vitro studies satisfying the inclusion criteria were probed which were meticulously screened and scrutinized for eligibility adhering to the 11 exclusion criteria. The quality assessment tool for in vitro studies (QUIN Tool) containing 12 criteria was employed to assess the risk of bias (RoB).

    RESULTS: A total of 48 studies assessing shear bond strength (SBS) and 15 studies evaluating tensile bond strength (TBS) were included in the qualitative synthesis. Concerning SBS, 33.4% moderate and 66.6% high RoB was observed. Concerning TBS, 26.8% moderate and 73.2% high RoB was discerned. Seventeen and two studies assessing SBS and TBS, respectively, were included in meta-analyses.

    CONCLUSIONS: Shear bond strength and TBS increased for the primed alloys. Cyclic disulfide primer is best-suited for noble alloys when compared with thiol/thione primers. Phosphoric acid- and phosphonic acid ester-based primers are opportune for base alloys.

    CLINICAL SIGNIFICANCE: The alloy-resin interface (ARI) would fail if an inappropriate primer was selected. Therefore, the selection of an appropriate alloy adhesive primer for an alloy plays a crucial role in prosthetic success. This systematic review would help in the identification and selection of a congruous primer for a selected alloy.

    Matched MeSH terms: Thiones*
  2. Shanmuga Sundara Raj S, Yamin BM, Yussof YA, Tarafder MT, Fun HK, Grouse KA
    Acta Crystallogr C, 2000 Oct;56 (Pt 10):1236-7.
    PMID: 11025309
    In the crystal structure of the title compound, C(8)H(10)N(2)S(2), the molecules are linked by N-H.S hydrogen bonds between the imino group and the thione-S atoms to form a chain along the b axis. The dithiocarbazate moiety is rotated by 85.8 (2) degrees with respect to the phenyl ring.
    Matched MeSH terms: Thiones
  3. Usman A, Razak IA, Chantrapromma S, Fun HK, Philip V, Sreekanth A, et al.
    Acta Crystallogr C, 2002 Nov;58(Pt 11):o652-4.
    PMID: 12415171
    The title compound, C(16)H(17)N(5)S, is in the thione form and crystallizes with two independent molecules in the asymmetric unit. In both molecules, the pentamethyleneimine five-membered ring adopts an envelope conformation, and in one of the molecules this ring shows positional disorder. The thione S and hydrazine N atoms are in the Z configuration with respect to the C-N bond.
    Matched MeSH terms: Thiones
  4. Rahima ZA, Abdul Halim SN, How FN
    Acta Crystallogr E Crystallogr Commun, 2015 Sep 1;71(Pt 9):o647.
    PMID: 26396883 DOI: 10.1107/S2056989015014462
    The title compound, C14H19NS2, crystallizes in the thione form with the presence of a C=S bond. The piperidine ring adopts a chair conformation. The dihedral angle between the essentially planar di-thio-carbamate and p-tolyl fragments is 74.46 (10)°.
    Matched MeSH terms: Thiones
  5. Tan YJ, Yeo CI, Halcovitch NR, Jotani MM, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2017 Apr 01;73(Pt 4):493-499.
    PMID: 28435705 DOI: 10.1107/S205698901700353X
    The title compound, (C6H11)3PS (systematic name: tri-cyclo-hexyl-λ(5)-phosphane-thione), is a triclinic (P-1, Z' = 1) polymorph of the previously reported ortho-rhom-bic form (Pnma, Z' = 1/2) [Kerr et al. (1977 ▸). Can. J. Chem. 55, 3081-3085; Reibenspies et al. (1996 ▸). Z. Kristallogr. 211, 400]. While conformational differences exist between the non-symmetric mol-ecule in the triclinic polymorph, cf. the mirror-symmetric mol-ecule in the ortho-rhom-bic form, these differences are not chemically significant. The major feature of the mol-ecular packing in the triclinic polymorph is the formation of linear chains along the a axis sustained by methine-C-H⋯S(thione) inter-actions. The chains pack with no directional inter-actions between them. The analysis of the Hirshfeld surface for both polymorphs indicates a high degree of similarity, being dominated by H⋯H (ca 90%) and S⋯H/H⋯S contacts.
    Matched MeSH terms: Thiones
  6. Razak IA, Usman A, Fun HK, Yamin BM, Keat GW
    Acta Crystallogr C, 2002 Feb;58(Pt 2):m122-3.
    PMID: 11828100
    In the title compound, [SbCl(2)(C(4)H(8)N(2)S)(2)]Cl, the coordination around the Sb atom can be described as distorted pseudo-octahedral. Both rings of the trimethylenethiourea ligands [alternatively 3,4,5,6-tetrahydropyrimidine-2(1H)-thione] adopt an envelope conformation. The molecules are connected into dimers in the ab plane by two intermolecular hydrogen bonds. The dimers are arranged into infinite one-dimensional chains along the a axis as a result of the Cl(-) ions forming intermolecular hydrogen bonds with three NH groups.
    Matched MeSH terms: Thiones
  7. Ramli SB, Ravoof TB, Tahir MI, Tiekink ER
    Acta Crystallogr E Crystallogr Commun, 2015 Jul 1;71(Pt 7):o475-6.
    PMID: 26279916 DOI: 10.1107/S205698901501107X
    In the title compound, C15H16N2S3 {systematic name: [({[(4-methyl-phen-yl)meth-yl]sulfan-yl}methane-thio-yl)amino][1-(thio-phen-2-yl)ethyl-idene]amine}, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0061 Å) and forms dihedral angles of 7.39 (10) and 64.91 (5)° with the thienyl and p-tolyl rings, respectively; the dihedral angle between these rings is 57.52 (6)°. The non-thione S atoms are syn, and with respect to the thione S atom, the benzyl group is anti. In the crystal, centrosymmetrically related mol-ecules self-associate via eight-membered {⋯HNCS}2 synthons. The dimeric aggregates stack along the a axis and are are consolidated into a three-dimensional architecture via methyl-C-H⋯π(benzene) and benzene-C-H⋯π(thien-yl) inter-actions.
    Matched MeSH terms: Thiones
  8. Kulkarni AD, Rahman ML, Mohd Yusoff M, Kwong HC, Quah CK
    Acta Crystallogr E Crystallogr Commun, 2015 Nov 1;71(Pt 11):1411-3.
    PMID: 26594522 DOI: 10.1107/S2056989015020101
    The title compound, C23H22FN5S, exists in a trans conformation with respect to the methene C=C and the acyclic N=C bonds. The 1,2,4-triazole-5(4H)-thione ring makes dihedral angles of 88.66 (9) and 84.51 (10)°, respectively, with the indole and benzene rings. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯π inter-actions, forming chains along [1-10]. The chains are linked via π-π inter-actions involving inversion-related triazole rings [centroid-centroid distance = 3.4340 (13) Å], forming layers parallel to the ab plane.
    Matched MeSH terms: Thiones
  9. Tan YS, Tiekink ER
    Acta Crystallogr E Crystallogr Commun, 2015 Oct 1;71(Pt 10):1143-6.
    PMID: 26594392 DOI: 10.1107/S2056989015016382
    The asymmetric unit of the title compound, {(C34H28FeP2)[Au(C5H8NS2)]2}, comprises half a mol-ecule, with the full mol-ecule being generated by the application of a centre of inversion. The independent Au(I) atom is coordinated by thiol-ate S and phosphane P atoms that define an approximate linear geometry [S-Au-P = 169.35 (3)°]. The deviation from the ideal linear is traced to the close approach of the (intra-molecular) non-coordinating thione S atom [Au⋯S = 3.1538 (8) Å]. Supra-molecular layers parallel to (100) feature in the crystal packing, being sustained by phen-yl-thione C-H⋯S inter-actions, with the non-coordinating thione S atom in the role of a dual acceptor. Layers stack with no specific inter-actions between them.
    Matched MeSH terms: Thiones
  10. Yusof ENM, Tahir MIM, Ravoof TBSA, Tan SL, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2017 Apr 01;73(Pt 4):543-549.
    PMID: 28435717 DOI: 10.1107/S2056989017003991
    The title di-thio-carbazate ester (I), C18H18N2S2 [systematic name: (E)-4-methyl-benzyl 2-[(E)-3-phenyl-allyl-idene]hydrazinecarbodi-thio-ate, comprises an almost planar central CN2S2 residue [r.m.s. deviation = 0.0131 Å]. The methyl-ene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the mol-ecule approximates mirror symmetry with the 4-tolyl group bis-ected by the plane. The configuration about both double bonds in the N-N=C-C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thio-amide synthons, {⋯HNCS}2, are formed via N-H⋯S(thione) hydrogen bonds. Connections between the dimers via C-H⋯π inter-actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter-action profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N-H⋯S hydrogen bonds is about 0.94 kcal mol(-1) more stable than that in (I).
    Matched MeSH terms: Thiones
  11. Tan SL, Azizan AHS, Jotani MM, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2019 Oct 01;75(Pt 10):1472-1478.
    PMID: 31636978 DOI: 10.1107/S2056989019012581
    In the title tri-substituted thio-urea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the mol-ecule [the S-C-N-C torsion angle is -49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hy-droxy-ethyl groups lying to either side of this plane. One hy-droxy-ethyl group is orientated towards the thio-amide functionality enabling the formation of an intra-molecular N-H⋯O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the mol-ecule is twisted. The experimental mol-ecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the mol-ecular packing, hydroxyl-O-H⋯O(hydrox-yl) and hydroxyl-O-H⋯S(thione) hydrogen bonds lead to the formation of a supra-molecular layer in the ab plane; no directional inter-actions are found between layers. The influence of the specified supra-molecular inter-actions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent inter-action plots; the inter-action energies point to the important stabilization provided by directional O-H⋯O hydrogen bonds.
    Matched MeSH terms: Thiones
  12. Aziz NA, Yusof EN, Ravoof TB, Tiekink ER
    Acta Crystallogr E Crystallogr Commun, 2015 Apr 1;71(Pt 4):o233-4.
    PMID: 26029430 DOI: 10.1107/S2056989015004764
    In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N-N bond is gauche [C-N-N-C = -117.48 (15)°]. Overall, the mol-ecule has the shape of the letter L. In the crystal packing, supra-molecular chains along the a axis are formed by N-H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phen-yl-tolyl C-H⋯π inter-actions; the layers stack along the c axis with no specific inter-actions between them.
    Matched MeSH terms: Thiones
  13. Mokhtaruddin NS, Ravoof TB, Tahir MI, Tiekink ER
    Acta Crystallogr E Crystallogr Commun, 2015 Apr 1;71(Pt 4):o253-4.
    PMID: 26029441 DOI: 10.1107/S2056989015005034
    In the title hydrate, C9H12N4S·H2O (systematic name: 3-methyl-1-{(E)-[(3-methyl-pyridin-2-yl)methyl-idene]amino}-thio-urea monohydrate), a small twist is noted between the pyridine ring and the rest of the organic mol-ecule [dihedral angle = 6.96 (5)°]. The imine and pyridine N atoms are syn, and the amine H atoms are anti. The latter arrangement allows for the formation of an intra-molecular N-H⋯N(imine) hydrogen bond. Both the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter forms O-H hydrogen bonds with the pyridine N and thione S atoms. These inter-actions lead to supra-molecular layers that stack along the a-axis direction with no specific inter-actions between them.
    Matched MeSH terms: Thiones
  14. Omar SA, Chah CK, Ravoof TBSA, Jotani MM, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2018 Feb 01;74(Pt 2):261-266.
    PMID: 29850067 DOI: 10.1107/S2056989018001330
    In the title di-thio-carbazate ester, C16H17N3S2 (systematic name: (Z)-{[(benzyl-sulfan-yl)methane-thio-yl]amino}[1-(6-methyl-pyridin-2-yl)ethyl-idene]amine), the central methyl-idenehydrazinecarbodi-thio-ate (C2N2S2) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thio-ester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intra-molecular hydrazine-N-H⋯N(pyrid-yl) hydrogen bond that closes an S(6) loop. In the crystal, phenyl-C-H⋯S(thione), methyl-ene-C-H⋯π(pyrid-yl), methyl-ene- and phenyl-C-H⋯π(phen-yl) contacts connect mol-ecules into supra-molecular layers propagating in the bc plane; the layers stack along the a axis with no directional inter-actions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intra-layer phenyl-H⋯H(pyrid-yl) contact upon the mol-ecular packing.
    Matched MeSH terms: Thiones
  15. Tan MY, Crouse KA, Ravoof TB, Tiekink ER
    Acta Crystallogr E Crystallogr Commun, 2015 Dec 1;71(Pt 12):o1047-8.
    PMID: 26870491 DOI: 10.1107/S2056989015023531
    In the title thio-semicarbazone compound, C18H18ClN3S, the CN3S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chloro-benzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. The conformation about the C=N bond is Z, and that about the C=C bonds is E. The imine N and ethyl N atoms are syn and are linked by an eth-yl-imine N-H⋯N hydrogen bond. This H atom also forms an inter-molecular hydrogen bond to the thione S atom, resulting in a supra-molecular helical chain propagating along the b axis. The chains are consolidated into a three-dimensional architecture by phenyl-C-H⋯Cl contacts and weak π-π inter-actions between centrosymmetrically related chloro-benzene rings [inter-centroid distance = 3.9127 (15) Å].
    Matched MeSH terms: Thiones
  16. Al-Omary FA, El-Emam AA, Ghabbour HA, Chidan Kumar CS, Quah CK, Fun HK
    Acta Crystallogr E Crystallogr Commun, 2015 Mar 1;71(Pt 3):o175-6.
    PMID: 25844234 DOI: 10.1107/S2056989015002273
    The title 1,3,4-oxa-diazole-2-thione derivative, C18H20N4OS2, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The 2-thienyl rings in both mol-ecules are rotationally disordered over two orientations by approximately 180° about the single C-C bond that connects it to the oxa-diazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in mol-ecules A and B, respectively. The 1,3,4-oxa-diazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (mol-ecule A), and 6.5 (3), 6.0 (9) and 55.30 (12)° (mol-ecule B) with the major and minor parts of the disordered thio-phene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the mol-ecules. The piperazine ring in both mol-ecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N-C-C-C torsion angles of -58.2 (3) and -66.2 (3)° in mol-ecules A and B, respectively. In the crystal, no inter-molecular hydrogen bonds are observed. The crystal packing features short S⋯S contacts [3.4792 (9) Å] and π-π inter-actions [3.661 (3), 3.664 (11) and 3.5727 (10) Å], producing a three-dimensional network.
    Matched MeSH terms: Thiones
  17. Al-Wabli RI, El-Emam AA, Alroqi OS, Chidan Kumar CS, Fun HK
    Acta Crystallogr E Crystallogr Commun, 2015 Feb 1;71(Pt 2):o115-6.
    PMID: 25878859 DOI: 10.1107/S2056989015000596
    The title compound, C18H20ClN3S, is a functionalized triazoline-3-thione derivative. The benzene ring is almost perpendic-ular to the planar 1,2,4-triazole ring [maximum deviation = 0.007 (1) Å] with a dihedral angle of 89.61 (5)° between them and there is an adamantane substituent at the 3-position of the triazole-thione ring. In the crystal, N-H⋯S hydrogen-bonding inter-actions link the mol-ecules into chains extending along the c-axis direction. The crystal packing is further stabilized by weak C-H⋯π inter-actions that link adjacent chains into a two-dimensional structure in the bc plane. The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio.
    Matched MeSH terms: Thiones
  18. Rusli AF, Kwong HC, Crouse KA, Jotani MM, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2020 Feb 01;76(Pt 2):208-213.
    PMID: 32071748 DOI: 10.1107/S2056989020000328
    The title hydrazine carbodi-thio-ate, C13H18N2OS2, is constructed about a central and almost planar C2N2S2 chromophore (r.m.s. deviation = 0.0263 Å); the terminal meth-oxy-benzene group is close to coplanar with this plane [dihedral angle = 3.92 (11)°]. The n-butyl group has an extended all-trans conformation [torsion angles S-Cm-Cm-Cm = -173.2 (3)° and Cm-Cm-Cm-Cme = 180.0 (4)°; m = methyl-ene and me = meth-yl]. The most prominent feature of the mol-ecular packing is the formation of centrosymmetric eight-membered {⋯HNCS}2 synthons, as a result of thio-amide-N-H⋯S(thio-amide) hydrogen bonds; these are linked via meth-oxy-C-H⋯π(meth-oxy-benzene) inter-actions to form a linear supra-molecular chain propagating along the a-axis direction. An analysis of the calculated Hirshfeld surfaces and two-dimensional fingerprint plots point to the significance of H⋯H (58.4%), S⋯H/H⋯S (17.1%), C⋯H/H⋯C (8.2%) and O⋯H/H⋯O (4.9%) contacts in the packing. The energies of the most significant inter-actions, i.e. the N-H⋯S and C-H⋯π inter-actions have their most significant contributions from electrostatic and dispersive components, respectively. The energies of two other identified close contacts at close to van der Waals distances, i.e. a thione-sulfur and meth-oxy-benzene-hydrogen contact (occurring within the chains along the a axis) and between methyl-ene-H atoms (occurring between chains to consolidate the three-dimensional architecture), are largely dispersive in nature.
    Matched MeSH terms: Thiones
  19. Tan SL, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2020 Jun 01;76(Pt 6):933-939.
    PMID: 32523767 DOI: 10.1107/S2056989020006829
    The title di-substituted thio-urea, C12H16N2O3S, has the hy-droxy-lethyl and ethyl benzoate substituents bound to the same amine-N atom, and is twisted, having a (+)syn-clinal conformation with the Namine-C-C-O(hydroxyl, carbon-yl) torsion angles of 49.39 (13) and 59.09 (12)°, respectively; the dihedral angle between the almost planar CN2S core and the pendent benzene ring is 69.26 (4)°. In the crystal, supra-molecular layers propagating in the ac plane are formed via a combination of hydroxyl-O-H⋯S(thione), amine-N-H⋯O(hydroxyl, carbon-yl) hydrogen-bonds. The layers stack along the b axis with inter-digitation of the benzene rings allowing the formation of π-π stacking [inter-centroid separation = 3.8722 (7) Å] and parallel C=O⋯π inter-actions. A computational chemistry study shows the conventional hydrogen bonding in the crystal leads to significant electrostatic stabilization but dispersion terms are also apparent, notably through the inter-actions involving the benzene residue.
    Matched MeSH terms: Thiones
  20. Tan SL, Jotani MM, Tiekink ERT
    Acta Crystallogr E Crystallogr Commun, 2020 Feb 01;76(Pt 2):155-161.
    PMID: 32071739 DOI: 10.1107/S2056989019017328
    In the title compound, C12H15N3O5S, a tris-ubstituted thio-urea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hy-droxy-ethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the mol-ecule, the S-C-N-C torsion angle of -47.8 (2)° indicates a considerable twist. As one of the hy-droxy-ethyl groups is orientated towards the thio-amide residue, an intra-molecular N-H⋯O hydrogen bond is formed which leads to an S(7) loop. A further twist in the mol-ecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CN2S chromophore and the 4-nitro-benzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) mol-ecular structures. In the crystal, O-H⋯O and O-H⋯S hydrogen bonds give rise to supra-molecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C-H⋯O, C-H⋯S and nitro-O⋯π. The nature of the supra-molecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent inter-action plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.
    Matched MeSH terms: Thiones
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