/* $Revision$ $Author$ $Date$
*
* Copyright (C) 2008 Miguel Rojas <miguelrojasch@yahoo.es>
*
* Contact: cdk-devel@lists.sourceforge.net
*
* This program is free software; you can redistribute it and/or
* modify it under the terms of the GNU Lesser General Public License
* as published by the Free Software Foundation; either version 2.1
* of the License, or (at your option) any later version.
*
* This program is distributed in the hope that it will be useful,
* but WITHOUT ANY WARRANTY; without even the implied warranty of
* MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
* GNU Lesser General Public License for more details.
*
* You should have received a copy of the GNU Lesser General Public License
* along with this program; if not, write to the Free Software
* Foundation, Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
*/
package org.openscience.cdk.reaction.mechanism;
import java.util.ArrayList;
import org.openscience.cdk.DefaultChemObjectBuilder;
import org.openscience.cdk.LonePair;
import org.openscience.cdk.annotations.TestClass;
import org.openscience.cdk.annotations.TestMethod;
import org.openscience.cdk.atomtype.CDKAtomTypeMatcher;
import org.openscience.cdk.exception.CDKException;
import org.openscience.cdk.graph.ConnectivityChecker;
import org.openscience.cdk.interfaces.IAtom;
import org.openscience.cdk.interfaces.IAtomType;
import org.openscience.cdk.interfaces.IBond;
import org.openscience.cdk.interfaces.IMapping;
import org.openscience.cdk.interfaces.IMolecule;
import org.openscience.cdk.interfaces.IMoleculeSet;
import org.openscience.cdk.interfaces.IReaction;
import org.openscience.cdk.reaction.IReactionMechanism;
import org.openscience.cdk.tools.manipulator.AtomContainerManipulator;
import org.openscience.cdk.tools.manipulator.BondManipulator;
/**
* This mechanism displaces the chemical bond to an Atom. Generating one with
* excess charge and the other with deficiency.
* It returns the reaction mechanism which has been cloned the IMolecule.
*
* @author miguelrojasch
* @cdk.created 2008-02-10
* @cdk.module reaction
*
*/
@TestClass(value="org.openscience.cdk.reaction.mechanism.HeterolyticCleavageMechanismTest")
public class HeterolyticCleavageMechanism implements IReactionMechanism{
/**
* Initiates the process for the given mechanism. The atoms to apply are mapped between
* reactants and products.
*
* @param moleculeSet The IMolecule to apply the mechanism
* @param atomList The list of atoms taking part in the mechanism. Only allowed two atoms.
* The first atom receives the positive charge charge and the second
* negative charge
* @param bondList The list of bonds taking part in the mechanism. Only allowed one bond
* @return The Reaction mechanism
*
*/
@TestMethod(value="testInitiate_IMoleculeSet_ArrayList_ArrayList")
public IReaction initiate(IMoleculeSet moleculeSet, ArrayList<IAtom> atomList,ArrayList<IBond> bondList) throws CDKException {
CDKAtomTypeMatcher atMatcher = CDKAtomTypeMatcher.getInstance(moleculeSet.getBuilder(), CDKAtomTypeMatcher.REQUIRE_EXPLICIT_HYDROGENS);
if (moleculeSet.getMoleculeCount() != 1) {
throw new CDKException("TautomerizationMechanism only expects one IMolecule");
}
if (atomList.size() != 2) {
throw new CDKException("HeterolyticCleavageMechanism expects two atoms in the ArrayList");
}
if (bondList.size() != 1) {
throw new CDKException("HeterolyticCleavageMechanism only expect one bond in the ArrayList");
}
IMolecule molecule = moleculeSet.getMolecule(0);
IMolecule reactantCloned;
try {
reactantCloned = (IMolecule) molecule.clone();
} catch (CloneNotSupportedException e) {
throw new CDKException("Could not clone IMolecule!", e);
}
IAtom atom1 = atomList.get(0);
IAtom atom1C = reactantCloned.getAtom(molecule.getAtomNumber(atom1));
IAtom atom2 = atomList.get(1);
IAtom atom2C = reactantCloned.getAtom(molecule.getAtomNumber(atom2));
IBond bond1 = bondList.get(0);
int posBond1 = molecule.getBondNumber(bond1);
if(bond1.getOrder() == IBond.Order.SINGLE)
reactantCloned.removeBond(reactantCloned.getBond(posBond1));
else
BondManipulator.decreaseBondOrder(reactantCloned.getBond(posBond1));
int charge = atom1C.getFormalCharge();
atom1C.setFormalCharge(charge+1);
// check if resulting atom type is reasonable
atom1C.setHybridization(null);
AtomContainerManipulator.percieveAtomTypesAndConfigureAtoms(reactantCloned);
IAtomType type = atMatcher.findMatchingAtomType(reactantCloned, atom1C);
if (type == null) return null;
charge = atom2C.getFormalCharge();
atom2C.setFormalCharge(charge-1);
reactantCloned.addLonePair(new LonePair(atom2C));
// check if resulting atom type is reasonable: an acceptor atom cannot be charged positive*/
atom2C.setHybridization(null);
AtomContainerManipulator.percieveAtomTypesAndConfigureAtoms(reactantCloned);
type = atMatcher.findMatchingAtomType(reactantCloned, atom2C);
if (type == null) return null;
IReaction reaction = DefaultChemObjectBuilder.getInstance().newReaction();
reaction.addReactant(molecule);
/* mapping */
for(IAtom atom:molecule.atoms()){
IMapping mapping = DefaultChemObjectBuilder.getInstance().newMapping(atom, reactantCloned.getAtom(molecule.getAtomNumber(atom)));
reaction.addMapping(mapping);
}
if(bond1.getOrder() != IBond.Order.SINGLE) {
reaction.addProduct(reactantCloned);
} else{
IMoleculeSet moleculeSetP = ConnectivityChecker.partitionIntoMolecules(reactantCloned);
for(int z = 0; z < moleculeSetP.getAtomContainerCount() ; z++){
reaction.addProduct(moleculeSetP.getMolecule(z));
}
}
return reaction;
}
}